2-Bromobenzoic acid → 2-Bromo-5-(chlorosulfonyl)benzoic acid

Participants

Reaction Steps

To chlorosulfonic acid (100 mL) cooled to 0° C. was added 2-bromobenzoic acid (20.0 g, 99.5 mmol) portionwise over 10 minutes. The reaction mixture was warmed to room temperature and then to reflux cautiously over 30 minutes in 10° C. increments, followed by reflux for 16 hours. After cooling to room temperature the solution was quenched in 1 mL portions into ice-water (2 L). Further ice was added as necessary to keep the temperature below 5° C. The resulting precipitate was filtered under vacuum and dried in a vacuum oven for 4 hours to give the title compound as a tan solid in 95% yield, 28.6 g.

Provenance & Evidence