Cyanogen Bromide → HCID 13656116, compound

Participants

Reaction Steps

A solution of 10.9 g (103 mmole) cyanogen bromide and 23 g (86 mmole) of 2-(3-phenyl-2,3-dihydrobenzofuran-3-yl)-N,N-dimethylethylamine in 500 ml CHCl3 was refluxed for 4 hours. The solvent was evaporated and the resultant oil warmed to reflux in 500 ml water. After cooling, the mixture was extracted with CH2Cl2 (2×1 liter), and the organics were washed with 1N HOAc (3×1 liter) and dried over K2CO3. Evaporation gave 20 g of an oil, which was chromatographed on 200 g silica gel using CH2Cl2 as an eluent to give 11 g of an oil which solidified on standing. Recrystallization from acetone/hexane gave 7.1 g (30%) of crystals, m.p. 88°-92°.

Provenance & Evidence