4-Fluorobenzoic Acid → HCID 14097619, compound

Participants

Reaction Steps

Methyl 4-(2-aminoethoxy)benzoate (19.5 g) and 14 g of p-fluorobenzoic acid were dissolved in 300 ml of N,N-dimethylformamide and 20.6 g of N,N'-dicyclohexylcarbodiimide was added thereto little by little with stirring at room temperature. The mixture was stirred for 8 hours, the resulting N,N'-dicyclohexylurea was removed by filtration, the filtrate was poured into ice water, and the mixture was extracted with ethyl acetate. The organic layer was washed with 10% hydrochloric acid, saturated potassium carbonate solution, and water. This was dried with anhydrous magnesium sulphate, concentrated in vacuo, the residue was crystallised with n-hexane, and the resulting 25.4 g of crystals were recrystallised from ethyl acetate/n-hexane to give 21.3 g (yield: 67%) of crystalline product. M.p. 105°-107° C.

Provenance & Evidence