1,2-dibromobenzene

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

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

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

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

Conditions: temp:80.01; pressure:0.00; stir:

Procedure: The general procedure A was followed using 1,2-dibromobenzene (58.6 uL, 0.5 mmol) and B2pin2 (126.9 mg, 0.5 mmol, 1.0 eq.) as starting material. The resulting mixture was allowed to stir 16 hours at 80 oC. 5j was obtained as colorless oil (178.2 mg, 98%) after purification by silica gel flash chromatography (EtOAc/PE=1:50 v/v).

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

Procedure: General procedure described for compounds 1 and 2 starting from 1,2-dibromobenzene and bromoacetyl bromide. Purified by column chromatography column (hexane:ethyl acetate 6:1), yield 13% m.p. 60-61° C., 1H-NMR (CDCl3): δ8.2 (s, 1H, Ar), 7.8 (d, 2H, Ar), 4.4 (s, 2H, CH2); 13C-NMR (CDCl3): δ189.7 (CO), 134.6 (CH), 134.4 (CH), 134.3 (C—CO), 132.0 (C—Br), 128.8(CH), 126.2 (C—Br), 30.4 (CH2); M/z (EI): 360, 358, 356, 354 (M+, 5, 14, 14, 5%), 265, 263, 261 (M-CH2Br, 62, 100, 65%); HPLC: Column μ Bondapack C18, 5 μm, 300 A, (300×3.9 mm), Purity 98%, r.t.=8.73 min, acetonitrile/H2O (0.05% H3PO4+0.04% Et3N) 50/50. Purified by column chromatography column (hexane:ethyl acetate 6:1), yield 13% m.p. 60-61° C., 1H-NMR (CDCl3): δ8.2 (s, 1H, Ar), 7.8 (d, 2H, Ar), 4.4 (s, 2H, CH2) Column μ Bondapack C18, 5 μm, 300 A, (300×3.9 mm), Purity 98%, r.t.=8.73 min, acetonitrile/H2O (0.05% H3PO4+0.04% Et3N) 50/50

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

Procedure: A 300-ml four-neck flask equipped with a stirring device, a condenser and a thermometer was prepared. Then, 80 g of 1,2-ethylene dichloride and 51 g (0.22 mols) of 1,2-dibromobenzene were placed in the flask, and 38 g (0.29 mols) of 60% fuming sulfuric acid was added thereto dropwise in a gentle stream of nitrogen gas and allowed to react therewith at 70° C. for 2 hours. After the resulting reaction product solution was cooled, a reaction product was filtered out, and then dried. Thus, 51 g of crude 3,4-dibromobenzenesulfonic acid was obtained. A 300-ml four-neck flask equipped with a stirring device, a condenser a thermometer was prepared was added to react After the resulting reaction product solution was cooled a reaction product was filtered out dried

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

Procedure: A 300-ml four-neck flask equipped with a stirring device, a condenser and a thermometer was prepared. Then, 90 g of 1,2-ethylene dichloride and 45 g (0.19 mols) of 1,2-dibromobenzene were placed in the flask, and 53.5 g (0.20 mols) of 30% fuming sulfuric acid was added thereto dropwise in a gentle stream of nitrogen gas and allowed to react therewith at 70° C. for 2 hours. After the resulting reaction product solution was cooled, a reaction product was filtered out, and then dried. Thus, 57 g of crude 3,4-dibromobenzenesulfonic acid was obtained. A 300-ml four-neck flask equipped with a stirring device, a condenser a thermometer was prepared was added to react After the resulting reaction product solution was cooled a reaction product was filtered out dried

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

Procedure: A 300-ml four-neck flask equipped with a stirring device, a condenser and a thermometer was prepared. Then, 90 g of 1,2-ethylene dichloride and 45 g (0.19 mols) of 1,2-dibromobenzene were placed in the flask, and 53.5 g (0.20 mols) of 30% fuming sulfuric acid was added thereto dropwise in a gentle stream of nitrogen gas and allowed to react therewith at 70° C. for 2 hours. After the resulting reaction product solution was cooled, a reaction product was filtered out, and then dried. Thus, 57 g of crude 3,4-dibromobenzenesulfonic acid was obtained. A 300-ml four-neck flask equipped with a stirring device, a condenser a thermometer was prepared was added to react After the resulting reaction product solution was cooled a reaction product was filtered out dried

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

Procedure: A 300-ml four-neck flask equipped with a stirring device, a condenser and a thermometer was prepared. Then, 120 g of 1,2-ethylene dichloride and 76 g (0.32 mols) of 1,2-dibromobenzene were placed in the flask, and 56 g (0.42 mols) of 60% fuming sulfuric acid was added thereto dropwise in a gentle stream of nitrogen gas and allowed to react therewith at 70° C. for 2 hours. After the resulting reaction product solution was cooled, a reaction product was filtered out and then dried. Thus, 95 g of crude 3,4-dibromobenzenesulfonic acid was obtained. A 300-ml four-neck flask equipped with a stirring device, a condenser a thermometer was prepared was added to react After the resulting reaction product solution was cooled a reaction product was filtered out dried

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

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