3,4-Dichlorobenzyl alcohol → HCID 71616386, compound

Participants

Reaction Steps

To a solution of 3,4-dichlorobenzyl alcohol (157 mg, 0.884 mmol) in tetrahydrofuran (3 mL) was added sodium hydride (60% dispersion in oil, 37 mg, 0.92 mmol). The reaction was stirred at room temperature for 45 minutes and heated to 55° C. for 30 minutes. The reaction mixture was cooled to room temperature and concentrated in vacuo. To the residue was added a solution of N-[(dimethylamino)sulfonyl]-2,4,5-trifluorobenzamide (Preparation 3, 100 mg, 0.354 mmol) in dimethyl sulfoxide (2 mL). The reaction mixture was stirred at room temperature for 3 hours and then partitioned between aqueous 2M hydrochloric acid (5 mL) and ethyl acetate (10 mL). The organic phase was separated and washed with a saturated aqueous solution of sodium chloride (10 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was triturated with diethyl ether, filtered and dried in vacuo to afford the title compound as a white solid (56 mg, 29%).

Provenance & Evidence