Dimethyl Sulfate → Methyl 5-iodo-2-methoxybenzoate

Participants

Reaction Steps

5-iodo-2-hydroxybenzoic acid (2.81 g, 10.6 mmol) was suspended in acetone (50 ml) and K2CO3 (6.77 g, 49.0 mmol) was added. The reaction was cooled in an ice water bath, and dimethylsulfate (2.4 ml, 25 mmol) was added via syringe. The reaction was warmed to room temperature, then heated to reflux, and stirred overnight. After 14.75 hours, the reaction was cooled to room temperature, diluted with water (150 ml), and stirred for 30 minutes. It was then extracted with EtOAc (3×50 ml), and the organic extracts were combined, dried over magnesium sulfate, filtered, concentrated, and purified on silica gel (Biotage instrument, 5% EtOAc/hexanes->100% EtOAc) to give methyl 5-iodo-2-methoxybenzoate (3.08 g, 99%).

Provenance & Evidence