Dimethylformamide → 139425-46-0

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 36 g of 5-fluorobenzothiazole in 100 ml of diethyl ether cooled to -70° C. was added dropwise over a 5 minute period 9.4 ml of a 2.5M solution of n-butyl lithium in hexane. The reaction mixture was allowed to warm to -50° C. for one hour and was then cooled to -78° C. Dry dimethylformamide (2.8 ml) was added dropwise and the reaction mixture allowed to warm to room temperature over a period of two hours. The reaction was diluted with 300 ml of diethyl ether and washed with 1N hydrochloric acid (1×40 ml), water (1×40 ml), a saturated sodium bicarbonate solution (1×40 ml) and dried over magnesium sulfate. The solvent was removed and the residual product flash chromatographed on silica (50% ethyl acetate--hexane; v:v) to give 24.7 g of the titled product, m.p. 105°-107° C.

Provenance & Evidence