Pyridine → HCID 69140603, compound

Participants

Reaction Conditions

Reaction Steps

This compound was prepared according to Ukita et al J. Med. Chem. 2001, 44, 2204. To a stirred mixture of 6-bromo-3-(2-methoxyphenyl)isobenzofuran-1(3H)-one (5.15 g, 16.1 mmol) in KOH (25% aqueous) (64.5 mL, 16.1 mmol) and pyridine (32.3 mL, 16.1 mmol) in a pressure tube was added powder potassium permanganate (3.83 g, 24.2 mmol). The reaction was heated at 100° C. After 4 h, LCMS showed ˜95% conversion to product. The reaction was cooled to rt. The mixture was filtered, and the solid residue was washed with water. The filtrate was acidified with concentrated HCl until pH=2. A sticky white solid was filtered off with the aid of water and dried to afford 5-bromo-2-(2-methoxybenzoyl)benzoic acid (4.2 g, 78% yield). m/z (ESI) 335.0 (M+H)+, 337.0 (M+3H)+.

Provenance & Evidence