Dimethylformamide → (2,3-dichlorophenyl)methanesulfonyl Chloride

Participants

Reaction Conditions

Reaction Steps

(2,3-dichlorophenyl)-methanesulfonic acid (260 mg, 1.0 mmole) was dissolved in 5 mL dry THF and cooled to 0° C. A catalytic drop of DMF was added followed by oxalyl chloride (0.44 mL, 5.0 mmole). The reaction mixture was allowed to warm to room temperature over 90 minutes and then filtered through Celite®, rinsing the Celite® with an additional 15 mL dry THF. The filtrate was evaporated to a volume of ca. 5 mL and then 5 mL water was added in small portions, cooling the vessel in a water bath. The mixture was extracted with 2×25 mL EtOAc and the combined organics were washed with saturated sodium bicarbonate, brine, and dried (MgSO4). Filtration and evaporation gives the crude product as a yellow oil. Chromatography on silica gel using a gradient of 5% EtOAc/Hexane to 30% EtOAc/Hexane gives 142 mg (2,3-dichlorophenyl)-methanesulfonyl chloride as a white solid.1H NMR (400 MHz, CHLOROFORM-D) δ ppm 5.09 (s, 2 H) 7.25 (t, J=7.96 Hz, 1 H) 7.45 (m, 1 H) 7.53 (dd, J=8.08, 1.52 Hz, 1 H)

Provenance & Evidence