Dimethyl Sulfoxide → 3-(3,4-Dichlorophenyl)-3-methylbutan-2-one

Participants

Reaction Steps

DMSO (14.7 mL, 205 mmol) was added dropwise to a solution of oxalyl chloride (9.0 mL, 103 mmol) in CH2Cl2 (200 mL) at −78° C. The reaction mixture was stirred for 30 min and a solution of 3-(3,4-dichlorophenyl)-3-methylbutan-2-ol (12 g, 51.4 mmol) in CH2Cl2 (50 mL) was added by cannula over 15 min. After stirring 30 min, Et3N (43 mL, 308 mmol) was added, and the reaction mixture was allowed to warm to room temperature over 1 h. Water (200 mL) was added, and the organic layer was separated. The aqueous layer was further extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude product was purified by column chromatography to give 3-(3,4-dichlorophenyl)-3-methylbutan-2-one (10.7 g, 89%). 1H NMR (400 MHz, CDCl3) δ 7.41 (d, 1H), 7.37 (m, 1H), 7.08 (d, 1H), 1.95 (s, 3H), 1.59 (s, 6H).

Provenance & Evidence