2-chloro-6-methylsulfanylbenzonitrile

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iron powder (0.5 g) and iodine (0.05 g) were added to a solution of 2-chloro-6-(methylsulphenyl)benzonitrile (10.0 g) in a mixture of carbon tetrachloride and dichloromethane. The mixture was warmed to 30° C. and bromine (9.5 g) was added. The mixture was heated at 55° C. for 5 hours. It was cooled, washed with aqueous sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane and treated with iron powder (0.5 g) and iodine (0.05 g). Bromine (6.5 g) was added and the mixture was heated at 55° C. for 5 hours. It was cooled and washed with sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane to give 3-bromo-2-chloro-6-(methylsulphenyl)benzonitrile (6.51 g) as an orange solid NMR (CDCl3) 2.5(s,3H) 7.0(d,1H) 7.65(d,1H). The mixture was heated at 55° C. for 5 hours It was cooled washed with aqueous sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane treated with iron powder (0.5 g) and iodine (0.05 g) Bromine (6.5 g) was added the mixture was heated at 55° C. for 5 hours It was cooled washed with sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iron powder (0.5 g) and iodine (0.05 g) were added to a solution of 2-chloro-6-(methylsulphenyl)benzonitrile (10.0 g) in a mixture of carbon tetrachloride and dichloromethane. The mixture was warmed to 30° C. and bromine (9.5 g) was added. The mixture was heated at 55° C. for 5 hours. It was cooled, washed with aqueous sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane and treated with iron powder (0.5 g) and iodine (0.05 g). Bromine (6.5 g) was added and the mixture was heated at 55° C. for 5 hours. It was cooled and washed with sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane to give 3-bromo-2-chloro-6-(methylsulphenyl)benzonitrile (6.51 g) as an orange solid NMR (CDCl3) 2.5(s,3H) 7.0(d, 1H) 7.65(d, 1H). The mixture was heated at 55° C. for 5 hours It was cooled washed with aqueous sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane treated with iron powder (0.5 g) and iodine (0.05 g) Bromine (6.5 g) was added the mixture was heated at 55° C. for 5 hours It was cooled washed with sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iron powder (0.5 g) and iodine (0.05 g) were added to a solution of 2-chloro-6-(methylsulphenyl)benzonitrile (10.0 g) in a mixture of carbon tetrachloride and dichloromethane. The mixture was warmed to 30° C. and bromine (9.5 g) was added. The mixture was heated at 55° C. for 5 hours. It was cooled, washed with aqueous sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane and treated with iron powder (0.5 g) and iodine (0.05 g). Bromine (6.5 g) was added and the mixture was heated at 55° C. for 5 hours. It was cooled and washed with sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane to give 3-bromo-2-chloro-6-(methylsulphenyl)benzonitrile (6.51 g) as an orange solid NMR (CDCl3) 2.5(s,3H) 7.0(d, 1H) 7.65(d, 1H). The mixture was heated at 55° C. for 5 hours It was cooled washed with aqueous sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane treated with iron powder (0.5 g) and iodine (0.05 g) Bromine (6.5 g) was added the mixture was heated at 55° C. for 5 hours It was cooled washed with sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iron powder (0.5 g) and iodine (0.05 g) were added to a solution of 2-chloro-6-(methylsulphenyl)benzonitrile (10.0 g) in a mixture of carbon tetrachloride and dichloromethane. The mixture was warmed to 30° C. and bromine (9.5 g) was added. The mixture was heated at 55° C. for 5 hours. It was cooled, washed with aqueous sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane and treated with iron powder (0.5 g) and iodine (0.05 g). Bromine (6.5 g) was added and the mixture was heated at 55° C. for 5 hours. It was cooled and washed with sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane to give 3-bromo-2-chloro-6-(methylsulphenyl)benzonitrile (6.51 g) as an orange solid NMR (CDCl3) 2.5(s,3H) 7.0(d,1H) 7.65(d,1H). The mixture was heated at 55° C. for 5 hours It was cooled washed with aqueous sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane treated with iron powder (0.5 g) and iodine (0.05 g) Bromine (6.5 g) was added the mixture was heated at 55° C. for 5 hours It was cooled washed with sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iron powder (0.5 g) and iodine (0.05 g) were added to a solution of 2-chloro-6-(methylsulphenyl)benzonitrile (10.0 g) in a mixture of carbon tetrachloride and dichloromethane. The mixture was warmed to 30° C. and bromine (9.5 g) was added. The mixture was heated at 55° C. for 5 hours. It was cooled, washed with aqueous sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane and treated with iron powder (0.5 g) and iodine (0.05 g). Bromine (6.5 g) was added and the mixture was heated at 55° C. for 5 hours. It was cooled and washed with sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane to give 3-bromo-2-chloro-6-(methylsulphenyl)benzonitrile (6.51 g) as an orange solid NMR (CDCl3) 2.5(s,3H) 7.0(d, 1H) 7.65(d, 1H). The mixture was heated at 55° C. for 5 hours It was cooled washed with aqueous sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane treated with iron powder (0.5 g) and iodine (0.05 g) Bromine (6.5 g) was added the mixture was heated at 55° C. for 5 hours It was cooled washed with sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iron powder (0.5 g) and iodine (0.05 g) were added to a solution of 2-chloro-6-(methylsulphenyl)benzonitrile (10.0 g) in a mixture of carbon tetrachloride and dichloromethane. The mixture was warmed to 30° C. and bromine (9.5 g) was added. The mixture was heated at 55° C. for 5 hours. It was cooled, washed with aqueous sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane and treated with iron powder (0.5 g) and iodine (0.05 g). Bromine (6.5 g) was added and the mixture was heated at 55° C. for 5 hours. It was cooled and washed with sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane to give 3-bromo-2-chloro-6-(methylsulphenyl)benzonitrile (6.51 g) as an orange solid NMR (CDCl3) 2.5(s,3H) 7.0(d, 1H) 7.65(d, 1H). The mixture was heated at 55° C. for 5 hours It was cooled washed with aqueous sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane treated with iron powder (0.5 g) and iodine (0.05 g) Bromine (6.5 g) was added the mixture was heated at 55° C. for 5 hours It was cooled washed with sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iron powder (0.5 g) and iodine (0.05 g) were added to a solution of 2-chloro-6-(methylsulphenyl)benzonitrile (10.0 g) in a mixture of carbon tetrachloride and dichloromethane. The mixture was warmed to 30° C. and bromine (9.5 g) was added. The mixture was heated at 55° C. for 5 hours. It was cooled, washed with aqueous sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane and treated with iron powder (0.5 g) and iodine (0.05 g). Bromine (6.5 g) was added and the mixture was heated at 55° C. for 5 hours. It was cooled and washed with sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane to give 3-bromo-2-chloro-6-(methylsulphenyl)benzonitrile (6.51 g) as an orange solid NMR (CDCl3) 2.5(s,3H) 7.0(d, 1H) 7.65(d, 1H). The mixture was heated at 55° C. for 5 hours It was cooled washed with aqueous sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane treated with iron powder (0.5 g) and iodine (0.05 g) Bromine (6.5 g) was added the mixture was heated at 55° C. for 5 hours It was cooled washed with sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iron powder (0.5 g) and iodine (0.05 g) were added to a solution of 2-chloro-6-(methylsulphenyl)benzonitrile (10.0 g) in a mixture of carbon tetrachloride and dichloromethane. The mixture was warmed to 30° C. and bromine (9.5 g) was added. The mixture was heated at 55° C. for 5 hours. It was cooled, washed with aqueous sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane and treated with iron powder (0.5 g) and iodine (0.05 g). Bromine (6.5 g) was added and the mixture was heated at 55° C. for 5 hours. It was cooled and washed with sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane to give 3-bromo-2-chloro-6-(methylsulphenyl)benzonitrile (6.51 g) as an orange solid NMR (CDCl3) 2.5(s,3H) 7.0(d, 1H) 7.65(d, 1H). The mixture was heated at 55° C. for 5 hours It was cooled washed with aqueous sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane treated with iron powder (0.5 g) and iodine (0.05 g) Bromine (6.5 g) was added the mixture was heated at 55° C. for 5 hours It was cooled washed with sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iron powder (0.5 g) and iodine (0.05 g) were added to a solution of 2-chloro-6-(methylsulphenyl)benzonitrile (10.0 g) in a mixture of carbon tetrachloride and dichloromethane. The mixture was warmed to 30° C. and bromine (9.5 g) was added. The mixture was heated at 55° C. for 5 hours. It was cooled, washed with aqueous sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane and treated with iron powder (0.5 g) and iodine (0.05 g). Bromine (6.5 g) was added and the mixture was heated at 55° C. for 5 hours. It was cooled and washed with sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane to give 3-bromo-2-chloro-6-(methylsulphenyl)benzonitrile (6.51 g) as an orange solid NMR (CDCl3) 2.5(s,3H) 7.0(d,1H) 7.65(d,1H). The mixture was heated at 55° C. for 5 hours It was cooled washed with aqueous sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane treated with iron powder (0.5 g) and iodine (0.05 g) Bromine (6.5 g) was added the mixture was heated at 55° C. for 5 hours It was cooled washed with sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iron powder (0.5 g) and iodine (0.05 g) were added to a solution of 2-chloro-6-(methylsulphenyl)benzonitrile (10.0 g) in a mixture of carbon tetrachloride and dichloromethane. The mixture was warmed to 30° C. and bromine (9.5 g) was added. The mixture was heated at 55° C. for 5 hours. It was cooled, washed with aqueous sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane and treated with iron powder (0.5 g) and iodine (0.05 g). Bromine (6.5 g) was added and the mixture was heated at 55° C. for 5 hours. It was cooled and washed with sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane to give 3-bromo-2-chloro-6-(methylsulphenyl)benzonitrile (6.51 g) as an orange solid NMR (CDCl3) 2.5(s,3H) 7.0(d,1H) 7.65(d,1H). The mixture was heated at 55° C. for 5 hours It was cooled washed with aqueous sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane treated with iron powder (0.5 g) and iodine (0.05 g) Bromine (6.5 g) was added the mixture was heated at 55° C. for 5 hours It was cooled washed with sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iron powder (0.5 g) and iodine (0.05 g) were added to a solution of 2-chloro-6-(methylsulphenyl)benzonitrile (10.0 g) in a mixture of carbon tetrachloride and dichloromethane. The mixture was warmed to 30° C. and bromine (9.5 g) was added. The mixture was heated at 55° C. for 5 hours. It was cooled, washed with aqueous sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane and treated with iron powder (0.5 g) and iodine (0.05 g). Bromine (6.5 g) was added and the mixture was heated at 55° C. for 5 hours. It was cooled and washed with sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane to give 3-bromo-2-chloro-6-(methylsulphenyl)benzonitrile (6.51 g) as an orange solid NMR (CDCl3) 2.5(s,3H) 7.0(d, 1H) 7.65(d, 1H). The mixture was heated at 55° C. for 5 hours It was cooled washed with aqueous sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane treated with iron powder (0.5 g) and iodine (0.05 g) Bromine (6.5 g) was added the mixture was heated at 55° C. for 5 hours It was cooled washed with sodium bisulphite, water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane