Sodium Hydroxide → HCID 178515621, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydroxide (10.9 g) was dissolved in methanol (110 ml), and a solution of hydroxylamine hydrochloride (4.2 g) in water (10 ml) was added dropwise thereto at 5° C. with stirring. A solution of α,β-dibromo-2,4-difluorocinnamic acid ethyl ester (19.6 g) in tetrahydrofuran (20 ml) was added dropwise to the mixture, and the resulting mixture was stirred at room temperature for 2 hours, followed by reflux for 5 hours. The solvent was evaporated under reduced pressure and the residue was poured into ice-cold water. The pH of the reaction mixture was adjusted to a value of 2 with conc. hydrochloric acid, and the reaction mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous NaCl solution, and the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: cyclohexane/ethyl acetate=1/1) to obtain the title compound (8.2 g, 79%) as colorless crystals.

Provenance & Evidence