Ethyl Acetate → Methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-iodobenzoate

Participants

Reaction Steps

To a solution of methyl 2-hydroxy-5-iodobenzoate (15 g, 53.9 mmol) in acetone (200 ml) was added 1-(bromomethyl)-4-fluorobenzene (9.95 ml, 81 mmol), potassium carbonate (14.91 g, 108 mmol) and the mixture was refluxed overnight. The mixture was allowed to cool and then filtered to remove the potassium carbonate. The solid potassium carbonate was washed with acetone (100 ml). The organics were combined and evaporated under reduced pressure on a buchi to give a solid. The solid was taken up into ethyl acetate (500 ml) and the organic phase was washed with water (2×200 ml), dried (MgSO4) and evaporated under reduced pressure on a buchi. The solid obtained was recrystallised from cyclohexane to yield the title compound as a white solid. 18.2 g.

Provenance & Evidence