Thionyl Chloride → N-[1-(4-Bromo-phenyl)-cyclopropanecarbonyl]-methanesulfonamide

Participants

Reaction Steps

1-(4-Bromo-phenyl)-cyclopropanecarboxylic acid (22 g, 91.3 mmol) and SOCl2 (13.6 mL, 183 mmol) in CH2Cl2 were heated together for 1.5 hours then evaporated to afford a dark oil. This oil was added via syringe over 30 minutes to a mixture of MeSO2NH2 (19 g, 200 mmol) in THF (250 mL) that was pre-treated at room temperature with NaH (60% in oil; 8.0 g, 200 mmol) for 1.5 hours. After a further 20 minutes, the mixture was poured into water, acidified and extracted with CH2Cl2, washed with water (2×) and evaporated to ˜100 mL. Hexane (300 mL) was added and the product collected by filtration to yield the title compound (25 g).

Provenance & Evidence