2-Bromobiphenyl → 2-Phenylbenzene-1-sulfonyl chloride

Participants

Reaction Conditions

Reaction Steps

2-Bromobiphenyl (2.33 g, 10 mmol) was dissolved in ether (10 ml) and cooled to -78° C. n-Butyllithium (2.5M solution in hexane, 4.8 ml, 12 mmol) was added dropwise under constant stirring and argon atmosphere. The resultant reaction mixture was stirred at -70° C. to -60° C. for 1 h. The reaction mixture was cooled to -78° C. and sulfuryl chloride (0.88 ml, 11 mmol) was added dropwise. After addition, the reaction mixture was allowed to attain ambient temperature slowly and stirred for 1 h. The reaction mixture was diluted with ethyl acetate (50 ml), washed with water and the organic layer dried over anhydrous MgSO4. Removal of the solvent under reduced pressure gave a crude product, which was purified by column chromatography, using hexane followed by 5% ethyl acetate in hexane as a eluent, to give 2-biphenylsulfonyl chloride as a solid (1.3 g, 51% yield).

Provenance & Evidence