Thiolation of benzylic bromideThiolation of benzylic bromide
SyntheticPage 631
Published Jul 17, 2013
α,α′-Dibromo-p-xylene (2 g, 3.78 mmol) and potassium carbonate (1.3 g, 9.40 mmol) were suspended in methanol (40 mL) under a steady flow of nitrogen. Thioacetic acid (0.65 mL, 9.23 mmol) was added slowly by syringe and the reaction was stirred at room temperature for 30 minutes, at which time a second portion of potassium carbonate (1.3 g, 9.40 mmol) was added. After 1 h the reaction was acidified to pH 6 by addition of 1M HCl, the reaction mixture was then extracted into CHCl3 (2 x 20 mL) and then washed with water (3 x 20 mL). The organic layer was dried over sodium sulfate, filtered and the solvents evaporated under reduced pressure to leave the product, as a white solid which was used without further purification (yield 0.39 g, 66%).