Acrylonitrile → 6-Bromo-2H-1-benzopyran-3-carbonitrile

Participants

Reaction Steps

A mixture of 2-hydroxy-5-bromobenzaldehyde XXIX (30 g, 0.15 mol), acrylonitrile (50 g, 0.75 mol), and 1,4-diazabicyclo[2.2.2]octane (Dabco, 4 g, 0.035 mol) was refluxed overnight. The reaction mixture was diluted with ethyl ether and washed with NaOH (1N), water, HCl (1N) and brine. The organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo to give 25 g of 6-bromo-2H-chromene-3-carbonitrile XXX (Yield 70%). MS: calc'd 237 (MH+), exp 237 (MH+).

Provenance & Evidence