Methyl 4-chloro-3-sulfamoylbenzoate → 2-chloro-5-(hydroxymethyl)Benzenesulfonamide

Participants

Reaction Steps

To a solution of methyl 3-(aminosulfonyl)-4-chlorobenzoate (950 mg, 3.8 mmol) in THF/EtOH (40 mL, 1:1), CaCl2 (843 mg, 7.6 mmol) and NaBH4 (575 mg, 15.2 mmol) were added in one portion respectively. The reaction mixture was stirred at room temperature for 6 hours, then quenched with water. 1 M aqueous citric acid (10 mL) was added to the mixture and extracted with EtOAc (3×100 mL). The extracts were combined, washed with brine, and dried (Na2SO4). The solvent was evaporated to afford the product (696 mg, 83%) as a white solid. MS (ES+) m/z 244 [M+Na]+.

Provenance & Evidence