Benzyl Bromide → HCID 66890793, compound

Participants

Reaction Steps

To a solution of methyl 3-fluoro-5-hydroxy-4-(methyloxy)benzoate (3.63 g, 18.1 mmol.) in DMF (25 mL) was added cesium carbonate (8.9 g, 27.2 mmol.) followed by benzyl bromide (2.8 mL, 23.6 mmol.) and the mixture was stirred at room temperature over 12 hours. The mixture was then partitioned with ethyl ether and water and the organic phase washed with water (3×) then saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. Filtration and concentration followed by purification of the residue by silica gel flash chromatography using 50% hexanes in chloroform as eluent afforded methyl 3-fluoro-4-(methyloxy)-5-[(phenylmethyl)oxy]benzoate (3.54 g, 67% yield) as a colorless solid after concentration of the pure fractions and drying in vacuo.

Provenance & Evidence