Chlorosuccinimide → Methyl 5-chloro-2-hydroxy-4-iodobenzoate

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 2-hydroxy-4-iodobenzoate (470 g, 1.7 mol) in acetic acid (1.9 L) was treated with N-chlorosuccinimide (250 g, 1.9 mol) and heated at 100-110° C. for 1 h. The reaction mixture was cooled to room temperature and the solid that precipitated was filtered, rinsed with acetic acid (250 mL) and water (2×500 mL), and dried on the filter under vacuum overnight to give the desired product (370 g, 70%) as a yellow powder. HPLC 95.8% pure @ 220 nm. LCMS for C8H7ClIO3 (M+H)+: m/z=312.9; Found: 313.0; 1H NMR (300 MHz, DMSO-d6): δ 10.5 (s, 1 H), 7.75 (s, 1 H), 7.57 (s, 1 H), 3.83 (s, 3 H).

Provenance & Evidence