Chlorosuccinimide → HCID 58368557, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 2-hydroxy-4-iodobenzoate (10.0 g, 36.0 mmol, from Aldrich) and N-chlorosuccinimide (5.76 g, 43.2 mmol) in acetic acid (40 mL) was heated at 100° C. for 1 hour and then cooled to room temperature overnight. The precipitate was collected by filtration and washed with ethyl acetate and then air dried to give the desired product. In addition, the filtrate was concentrated to dryness and partitioned between water and ethyl acetate. The organic phase was separated, washed with brine, dried over sodium sulfate and concentrated to dryness. The residue was purified on silica gel, eluting with 0 to 20% ethyl acetate in hexane, to give additional desired product (total 9.03 g, 82%). LCMS calculated for C8H7ClIO3 (M+H)+: m/z=312.9; Found: 313.0.

Provenance & Evidence