Sodium Hydroxide → 4-Chloro-2-fluoroaniline

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a suspension of 718 g (3.8 moles) of 4-chloro-2-fluoroacetanilide in 2653 mL of ethanol was stirred as a solution of 304 g (7.6 moles) of sodium hydroxide in 1075 mL of water was added. Upon completion of addition the reaction mixture was warmed to 80° C. during a 2.3 hour period. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure to a volume of approximately 2000 mL. The concentrate was dissolved in 2000 mL of ethyl acetate and washed with 500 mL of water. The organic layer was concentrated under reduced pressure to a residual oil. The oil was filtered to remove a solid, then distilled under reduced pressure to yield 329 g of 4-chloro-2-fluoroaniline; b.p. 93°-100° C./16-20 mm.

Provenance & Evidence