(4-bromophenyl)-pentafluoro-lambda6-sulfane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of n-butyllithium (9.4 ml of a 1.6 M solution in hexane) was added to a stirred solution of 4-bromophenylsulphur pentafluoride (3.87 g) in ether at -78° C. under an inert atmosphere. After maintaining at -78° C. for 1 hour, solid carbon dioxide (20 g) was added and the mixture allowed to warm to 5° C. during 1.5 hours. Hydrochloric acid (2 M) was added, the mixture stirred for 0.5 hour and the organic phase separated and itself extracted with sodium carbonate solution. The basic extract was washed (ether) and acidified (hydrochloric acid). The precipitated solid was extracted (ether), dried (magnesium sulphate) and evaporated. The residue was triturated (hexane) to give 4-pentafluorosulphanylbenzoic acid as a fawn solid (1.2 g), m.p.188-190° C. to warm to 5° C. during 1.5 hours the organic phase separated itself extracted with sodium carbonate solution The basic extract was washed (ether) The precipitated solid was extracted (ether) dried (magnesium sulphate) evaporated The residue was triturated (hexane)

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

Procedure: 8.5 g of p-bromophenyl-sulfur pentafluoride and 20 ml of piperidine are added to a mixture of 8.5 g of 4-pentoxyphenylacetylene, 20 ml of piperidine, 420 mg of triphenylphosphine-palladium(II) chloride and 30 mg of copper iodide, and the combined mixture is heated for 20 hours. Concentration and working up in the customary manner gives 4-(2-(4-pentoxyphenyl)-ethynyl)-phenyl-sulfur pentafluoride. the combined mixture is heated for 20 hours Concentration

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

Procedure: A mixture of 18.3 g of 4-bromophenyl-sulfur pentafluoride and 50 ml of tetrahydrofuran is added to a mixture of the organozinc compound prepared from 28.7 g of 1-bromo-4-(trans-4-propylcyclohexyl)-cyclohexane and 7 g of zinc, 13 g of nickel(II) chloride and tetrahydrofuran, and the mixture is heated at the boil for 5 hours. Working up in the customary manner gives 4-(trans-4-(trans-4-propylcyclohexyl)-cyclohexyl)-phenyl-sulfur pentafluoride. the mixture is heated at the boil for 5 hours

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Stir 1-bromo-4-pentafluorosulfanylbenzene (100 mg) together with bis(pinacolato)diboron (90 mg), potassium acetate (104 mg) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (43 mg) in DMF (2 ml) at 80° C. for 2 h. Allow the reaction mixture to cool, then add Na2CO3 (225 mg), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (43 mg), water (0.7 ml) and (S)-tert-butyl 4-(3-bromophenyl)-1,4-dimethyl-6-oxo-tetrahydropyrimidin-2(1H)-ylidenecarbamate (240 mg). Stir the mixture at 80° C. for 3 h. Allow the reaction mixture to cool, dilute with EtOAc (20 ml) and wash with water (2×5 ml). Dry the organic layer (MgSO4), filter and evaporate the filtrate. Chromatograph the residue on a silica gel column and elute with EtOAc/hexanes to afford the product, (S)-tert-butyl 4-(4′-pentafluorosulfanylbiphenyl-3-yl)-1,4-dimethyl-6-oxotetrahydropyrimidin-2(1H)-ylidenecarbamate. to cool to cool wash with water (2×5 ml) Dry the organic layer (MgSO4) filter evaporate the filtrate Chromatograph the residue on a silica gel column and elute with EtOAc/hexanes

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of n-butyllithium (9.4 ml of a 1.6M solution in hexane) was added to a stirred solution of 4-bromophenylsulphur pentafluoride (3.87 g) in ether at -78° C. under an inert atmosphere. After maintaining at -78° C. for 1 hour, solid carbon dioxide (20 g) was added and the mixture allowed to warm to 5° C. during 1.5 hours. Hydrochloric acid (2M) was added, the mixture stirred for 0.5 hour and the organic phase separated and itself extracted with sodium carbonate solution. The basic extract was washed (ether) and acidified (hydrochloric acid). The precipitated solid was extracted (ether), dried (magnesium sulphate) and evaporated. The residue was triturated (hexane) to give 4-pentafluorosulphanylbenzoic acid as a fawn solid (1.2 g), m.p.188-190° C. to warm to 5° C. during 1.5 hours the organic phase separated itself extracted with sodium carbonate solution The basic extract was washed (ether) The precipitated solid was extracted (ether) dried (magnesium sulphate) evaporated The residue was triturated (hexane)

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

Procedure: The requisite {cis-5-[4-(pentafluoro-λ6-sulfanyl)phenyl]tetrahydrofuran-2-yl}methanol was prepared via Suzuki reaction of (5-formylfuran-2-yl)boronic acid with 1-bromo-4-(pentafluoro-λ6-sulfanyl)benzene, followed by hydrogenation in the presence of ruthenium(IV) oxide hydrate.

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of n-butyllithium (9.4 ml of a 1.6 M solution in hexane) was added to a stirred solution of 4-bromophenylsulphur pentafluoride (3.87 g) in ether at -78° C. under an inert atmosphere. After maintaining at -78° C. for 1 hour, solid carbon dioxide (20 g) was added and the mixture allowed to warm to 5° C. during 1.5 hours. Hydrochloric acid (2 M) was added, the mixture stirred for 0.5 hour and the organic phase separated and itself extracted with sodium carbonate solution. The basic extract was washed (ether) and acidified (hydrochloric acid). The precipitated solid was extracted (ether), dried (magnesium sulphate) and evaporated. The residue was triturated (hexane) to give 4-pentafluorosulphanylbenzoic acid as a fawn solid (1.2 g), m.p.188-190° C. to warm to 5° C. during 1.5 hours the organic phase separated itself extracted with sodium carbonate solution The basic extract was washed (ether) The precipitated solid was extracted (ether) dried (magnesium sulphate) evaporated The residue was triturated (hexane)

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

Procedure: 8.5 g of p-bromophenyl-sulfur pentafluoride and 20 ml of piperidine are added to a mixture of 8.5 g of 4-pentoxyphenylacetylene, 20 ml of piperidine, 420 mg of triphenylphosphine-palladium(II) chloride and 30 mg of copper iodide, and the combined mixture is heated for 20 hours. Concentration and working up in the customary manner gives 4-(2-(4-pentoxyphenyl)-ethynyl)-phenyl-sulfur pentafluoride. the combined mixture is heated for 20 hours Concentration

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

Procedure: 8.5 g of p-bromophenyl-sulfur pentafluoride and 20 ml of piperidine are added to a mixture of 8.5 g of 4-pentoxyphenylacetylene, 20 ml of piperidine, 420 mg of triphenylphosphine-palladium(II) chloride and 30 mg of copper iodide, and the combined mixture is heated for 20 hours. Concentration and working up in the customary manner gives 4-(2-(4-pentoxyphenyl)-ethynyl)-phenyl-sulfur pentafluoride. the combined mixture is heated for 20 hours Concentration

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

Procedure: A mixture of 18.3 g of 4-bromophenyl-sulfur pentafluoride and 50 ml of tetrahydrofuran is added to a mixture of the organozinc compound prepared from 28.7 g of 1-bromo-4-(trans-4-propylcyclohexyl)-cyclohexane and 7 g of zinc, 13 g of nickel(II) chloride and tetrahydrofuran, and the mixture is heated at the boil for 5 hours. Working up in the customary manner gives 4-(trans-4-(trans-4-propylcyclohexyl)-cyclohexyl)-phenyl-sulfur pentafluoride. the mixture is heated at the boil for 5 hours