(5-Bromo-4-methoxy-3-methyl-benzofuran-2-yl)-methanol → HCID 68713008, compound

Participants

Reaction Steps

A suspension of (5-bromo-4-methoxy-3-methyl benzofuran-2-yl)-methanol (0.31 g; 1.1 mmol, Example 136, Step 1) and CuCN (0.21 g; 2.3 mmol; 2 eq) in N-methylpyrrolidinone (1.5 mL) was subjected to microwave radiation at 200° C. for 10 minutes. The reaction was diluted with water and ethyl acetate (10 mL each) and filtered. The layers were separated and the aqueous phase was washed with a second portion of ethyl acetate. The combined organic layers were washed twice with water and once with brine. After drying over magnesium sulfate, filtration and concentration in vacuo gave the crude product. Chromatography on silica gel, eluting with 20% to 30% ethyl acetate/hexanes gave pure 2-hydroxymethyl-4-methoxy-3-methyl benzofuran-5-carbonitrile (0.17 g; 67% yield).

Provenance & Evidence