Hydrochloric Acid → 2-Cyano-6,11-dihydro-11-oxodibenz[b,e]oxepin

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Reaction Conditions

Reaction Steps

Reflux 43 gm. (0.1488 mole of 2-bromo-6,11-dihydro-11-oxodibenz[b,e]oxepin and 16 gm. (0.178 mole, 20% excess) of cuprous cyanide in 150 cc. of N,N-dimethylformamide for 24 hours. Cool to 100° C. and pour into a solution of 100 gm. of ferric chloride in 140 cc. of 5% aqueous hydrochloric acid with stirring. Keep the mixture at 70° C. for 30 minutes cool, filter and wash the solids with water. Dissolve the solids in methylene chloride and purify by filtering through a short column of silica gel (m.p. 160°-161° C.).

Provenance & Evidence