Methyl iodide → Methyl 2-bromo-5-iodobenzoate

Participants

Reaction Steps

Methyl iodide (13 g, 91.5 mmol) is added to slurry of 2-bromo-5-iodobenzoic acid (23 g, 70.4 mmol) and K2CO3 (14.6 g, 106 mmol) in DMF (50 mL) at room temperature. After TLC shows complete consumption of the starting material, the reaction is diluted with Et2O and washed three times with a saturated aqueous solution of NaCl. The combined aqueous layers are extracted once with fresh Et2O and once with EtOAc. The organic layers are combined, dried with Na2SO4, filtered and concentrated to an oil. The oil is diluted with a minimal amount of Et2O and filtered through a plug of silica. The silica is rinsed with a 20% ether/hexanes mixture. The eluents are concentrated in vacuo to give 2-bromo-5-iodobenzoic acid methyl ester as a solid.

Provenance & Evidence