3,5-Bis(trifluoromethyl)benzenesulphonyl chloride → Benzhydrol

Participants

Reaction Steps

Benzhydrol 2-(2-amino-4-trifluoromethylphenoxy)benzoate (4 g, 8.6 mmol) was dissolved in pyridine (25 mL) and stirred under argon at room temperature. 3,5-bis(trifluoromethyl)benzenesulfonyl chloride (4.05 g, 12.9 mmol) was added in portions, and the mixture stirred for 16 h. The solvent was evaporated, and the residue was purified by flash chromatography (silica gel, ethyl acetate/hexane) to give the title compound as a minor product. 1H NMR (250 MHz, CDCl3) δ8.60 (s, 4H), 8.21 (dd, 1H), 8.10 (s, 2H), 7.00-7.61 (m, 16H), 6.58 (d, 1H). The major product from this reaction was benzhydrol 2-[2-[3,5-bis(trifluoromethyl)phenylsulfonamido]-4-trifluoromethyl-phenoxy]benzoate.

Provenance & Evidence