3-Methoxybenzyl bromide → HCID 57825136, compound

Participants

Reaction Steps

To a solution of 3-[1-(4-methoxy-3-methyl-phenyl)-vinyl]-phenol (400 mg, 1.67 mmol, 1.0 eq) in 3 mL of dry N,N-dimethylformamide, anhydrous cesium carbonate was added (1.08 g, 3.33 mmol, 2.0 eq.) and the mixture was stirred for 20 min at room temperature. After this time, 3-methoxybenzylbromide (167 mg, 0.832 mmol, 1.2 eq.) was added and the resulting mixture was further stirred for 16 hours at 50° C. The reaction mixture was examined LC-MS which showed>90% conversion to the desired product. The reaction mixture was cooled to room temperature, 10 mL of water was added and the mixture was extracted with DCM. The organic fraction was dried over sodium sulfate and the crude product was purified by flash chromatography eluting with cyclohexane/ethylacetate (100:0 to 90:10). 408 mg of clean product was obtained as colorless liquid (yield: 95%)

Provenance & Evidence