Methanol → Methyl 3-hydroxy-4-iodobenzoate

Participants

Reaction Steps

3-Hydroxy-4-iodobenzoic acid (12.55 g, 47.5 mmol) is dissolved in MeOH (200 mL), treated slowly dropwise with thionyl chloride (32.3 mL, 442.9 mmol) at rt, then heated to reflux for 20 h. The mixture is concentrated to dryness and partitioned between CH2Cl2 (100 mL) and saturated NaHCO3 (50 mL). Not all of the residue is solubilized, so the mixture is filtered and the solid is washed with a small amount of CH2Cl2 and MeOH. The original filtrate and the organic washes are combined, concentrated to dryness, dissolved in 10% MeOH/CH2Cl2 (200 mL), diluted with water (50 mL) and the layers separated. The organics are washed with saturated NaHCO3 (2×50 mL), then water (50 mL), dried over anhydrous Na2SO4 and concentrated to a tan solid. This solid is triturated with CH2Cl2 (50 mL) and filtered. The two solids are combined to afford 9.4 g (70%) of methyl 3-hydroxy-4-iodobenzoate as a beige solid. HRMS (FAB) calcd for C8H7IO3+H1: 278.9520, found 278.9521.

Provenance & Evidence