Dimethylformamide → 3-Chloro-3-(2-chlorophenyl)prop-2-enenitrile

Participants

Reaction Conditions

Reaction Steps

25 ml of DMF were cooled to 0° C. and POCl3 (4.95 g, 32.3 mmol, 2 eq.) added dropwise. The reaction was stirred 30 min at 0° C. and a solution of 2-chloro-acetophenone (2.5 g, 16.17 mmol, 1 eq.) in 15 ml of DMF was added. Once all added the reaction was warmed to 50° C. and stirred for 8 h. The mixture was cooled to 0° C. and hydroxylamine hydrochloride (4.49 g, 6.68 mmol, 4 eq.) was added by portions very carefully (exothermic). Once all added the reaction was stirred at r.t. for 2 h and quenched with H2O. The medium was basified until pH 2-3 was reached with 1N aq. NaOH and extracted with ethylacetate. The organic layer was washed with brine and dried over MgSO4. Removal of all volatiles under reduced pressure afforded 3-chloro-3-(2-chlorophenyl)acrylonitrile (2.01 g, 60% yield) as a mixture of isomers which was used without further purification.

Provenance & Evidence