Benzyl Bromide → Methyl 3-(benzyloxy)-4-iodobenzoate

Participants

Reaction Conditions

Reaction Steps

The mixture of 3-hydroxy-4-iodo-benzoic acid methyl ester (1.2 g, 4.3 mmol), potassium carbonate (1.78 g, 13 mmol), acetone (15.0 mL), benzyl bromide (1.5 g, 8.6 mmol), and TBAI (0.05 g) is heated to 50° C. overnight. The solvent is removed under reduced pressure. The residue is partitioned between EtOAc (30 mL) and water (30 mL). The organic phase is washed with brine (20 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography to afford the title compound as white solid (1.58 g, 99%). LC-ES/MS m/e 386.0 (M+18).

Provenance & Evidence