1,3-Dibromopropane → HCID 21258492, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-naphthylacetonitrile (10 g) and 1,3-dibromopropane (144 g) in a mixture of ether (350 ml) and dimethylsulphoxide (150 ml) was added dropwise at 20-25° C. under nitrogen over 2 hours to a stirred mixture of finely-powdered potassium hydroxide (150 g), 18-Crown-6 (1.3 g) and dimethylsulphoxide (570 ml). After the addition was complete, the mixture was cooled to 15° C. and quenched by the slow addition of water (330 ml). Ether (330 ml) was added, and the mixture was filtered through Hyflo Supercel filtration aid. The filter pad was washed well with ether, then the aqueous layer of the filtrate was separated, diluted with water (500 ml), and washed well with ether. All of the ethereal solutions were combined, washed with water (3×100 ml), and the solvents were removed in vacua. The residue was triturated with ethanol (100 ml) and the resulting solid was collected by filtration and dried in vacua to give 1-(2-naphthyl)cyclobutanecarbonitrile as a white solid (48.7 g), which was used without further purification.

Provenance & Evidence