Methyl phenyl sulfone → Benzenesulfonamide

Participants

Reaction Steps

A solution of (phenylsulfonyl)methane (10 mmol) in 5 mL of THF at 0° C. was treated with 4.5 mL (12.6 mmol) of methylmagnesium chloride (2.8M in THF), and the resulting solution was stirred at room temperature for 30 minutes. The solution was cooled to 0° C., treated with 15 mL (15 mmol) of tributylborane (1M in THF), stirred at room temperature for 30 minutes, and then stirred at reflux for 18 hours. To the resulting mixture at 0° C. was added 5.7 g of sodium acetate, 25 mL of water, and 3.95 g of hydroxylamine-O-sulfonic acid; the resulting mixture was stirred at room temperature for 3 hours. The organic layer was diluted with ethyl acetate, washed with saturated NaHCO3 and then brine, dried (MgSO4), filtered, and concentrated in vacuo. Purification by silica gel chromatography gave 1.06 g (67%) of phenylsulfonamide.

Provenance & Evidence