Pyridine → HCID 20187037, compound

Participants

Reaction Steps

To a stirred solution of 4.2 grams (0.038 mole) of 3-fluoroaniline in 35 ml of chloroform was added 3.1 ml of pyridine. The reaction mixture was cooled to 0° and 7.0 grams (0.038 mole) of [Z]-2-bromo-2-butenoyl chloride (Step C product) was added dropwise at such a rate that the reaction mixture temperature did not exceed 10°. Upon completion of addition, the reaction mixture was stirred at 0° for one hour, then was allowed to warm to ambient temperature where it was stirred for 16 hours. The reaction mixture was washed with 10 ml of water, two portions of 10 ml each of aqueous 0.1N hydrochloric acid, 10 ml of water, and finally 10 ml of an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was crystallized from hexane using silica gel as a decolorant to give 6.7 grams of [Z]-2-bromo-N-(3-fluorophenyl)-2-butenamide; mp 44°-45.5°.

Provenance & Evidence