2-(4-Bromobenzyl)malonic acid → 3-(4-Bromophenyl)propionic acid

Participants

Reaction Steps

A solution of 2-(4-bromobenzyl)malonic acid (18 g, 66.18 mmol, 1.00 equiv) in dimethylsulfoxide (50 mL) was stirred at 160° C. for 2 h. The reaction mixture was cooled to room temperature and the product was precipitated by the addition of 200 mL ice and water. The solid was collected by filtration, washed with 1×50 mL of water and dried in a vacuum oven to give 14.8 g (98%) of 3-(4-bromophenyl)propanoic acid as a white solid. LC-MS: (ES, m/z): 229 [M+H]+. 1HNMR (400 MHz, DMSO-d6, ppm): δ 7.45 (d, J=8.0 Hz, 2H), 7.21 (d, J=8.0 Hz, 2H), 2.82-2.77 (m, 2H), 2.55-2.51 (m, 2H).

Provenance & Evidence