Dimethylformamide → HCID 54215258, compound

Participants

Reaction Steps

A solution of cuprous cyanide (2.7 g, 30.5 mmol) and 1-(4-bromo-2-methylphenyl)-2-(9H-xanthen-9-ylmethyl)ethanone (10 g, 25.4 mmol) in dry dimethylformamide (80 ml) was heated to reflux under an atmosphere of nitrogen. After 24 h, further cuprous cyanide (2 g, 22.3 mmol) was added and reflux continued for another 20 h. The reaction mixture was cooled and a solution of ferric chloride (8.6 g, 52.9 mmol) in aqueous hydrochloric acid (2M, 200 ml) added. The resulting solution was diluted with water (400 ml) and extracted twice with diethyl ether, the combined extracts were washed with water (5×) and a saturated solution of sodium chloride. The organic phase was dried over magnesium sulphate, filtered and evaporated to a yellow oil. Purified on flash silica eluting with hexane-dichloromethane (4:1 then 3:2 then 1:1) to give 1-(4-cyano-2-methylphenyl)-2-(9H-xanthen-9-ylmethyl)ethanone as a yellow oil. Sample crystallised from hexane m.p. 138°-141° C.

Provenance & Evidence