1,2-Dibromoethane → 1-(3-Trifluoromethyl-phenyl)-cyclopropanecarbonitrile

Participants

Reaction Steps

To a mixture of 3-(trifluoromethyl)phenylacetonitrile (18.5 g, 0.1 mole), 1,2-dibromoethane (56.4 g, 0.3 mole) and triethylbenzylammonium chloride (TEBA) (1.0 g), there was added 40 ml of 50% sodium hydroxide solution at room temperature. The exothermic reaction mixture was vigorously stirred overnight. The reaction mixture was diluted with water (100 ml) and extracted with ether (4×100 ml). The organic layer was washed with water (3×50 ml), brine (50 ml) and dried over magnesium sulfate. The solvent was removed and the product was distilled under reduced pressure (B.P. 92°-94° C. at 0.4 mm Hg) to give a 16.7 g of product (79% yield). ##STR4## where Xn is 4-chloro; 2-bromo; 3-bromo; 2-iodo; 3-iodo; 4-iodo; 3-carboxylic acid; 3-NO3 ; 2,3-benzo.

Provenance & Evidence