Water → 5-Bromo-2-chloro-4-(methoxycarbonyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 2-bromo-5-chloro-4-methylbenzoate (39.53 g, 0.15 mol), 18-Crown-6 (3.95 g), tert-butyl alcohol (350 mL), and water (750 mL) was combined together with mechanical stirring. The reaction mixture was heated to reflux and monitored by TLC. After refluxing overnight, the reaction was cooled to 55° C. and filtered. The filter cake was washed with hot water (2×100 mL, 50° C.). The filtrate was neutralized with 18% hydrochloric acid to pH 1 and stored in a refrigerator (0˜5° C.) for 3 h. It was filtered, and then washed with ice water (2×50 mL) and petroleum ether (2×50 mL). The filter cake was dried under vacuum to give the title compound as a white crystalline solid. Yield: 32.1 g (73%). 1H-NMR (DMSO-d6, 300 MHz): δ 8.10 (s, 1H), 7.89 (s, 1H), 3.86 (s, 3H).

Provenance & Evidence