Hydrochloric Acid → {[7-Chloro-3-(4-fluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetic acid

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4.0 g NaH in 50 ml DMF, a solution of 20 g of 2,3-dichloro-4-hydroxy-4'-fluorobenzophenone oxime in 100 ml of DMF is added dropwise in an atmosphere of N2. The reaction mixture is heated to an internal temperature of 96° C. for 2 hours. The reaction mixture is cooled to 40° C. and 12.3 g of ethyl bromoacetate is added dropwise and the mixture is stirred for one hour. Twenty milliliters of 50% NaOH and 100 ml of water is added and the reaction is heated at 80°-90° C. for one hour. Concentrated HCl is added until the reaction mixture is acidic and the mixture is stirred for one half hour and water added. A solid product is collected by filtration and recrystallized to give a pure product of {[7-chloro-3-(4-fluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetic acid, mp 233°-237° C.

Provenance & Evidence