Chlorosuccinimide → 4,5-Dichloro-2-methoxybenzoic acid

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Reaction Steps

To a solution of 4-chloro-2-methoxybenzoic acid (5 g, 26.8 mmol) in 200 mL of acetonitrile was added N-chlorosuccinimide (17.9 g, 134 mmol). The mixture was allowed to stir for 72 hours at ambient temperature and was quenched with 50 mL of H2O. The layers were separated and the aqueous layer was extracted with three 25 mL portions of CH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via column chromatography (SiO2, 25% hexanes in ethyl acetate) afforded the title compound. MS (DCI/NH3) m/z 238 (M+NH4)+.

Provenance & Evidence