Water → 2-fluoro-N-methoxycarbonylaniline

Participants

Reaction Steps

2-Fluoroaniline (10.0 mL, 0.104 mol) was dissolved in ethyl acetate (40 mL) to prepare a solution. Pyridine (10.0 mL, 0.124 mol) was added to the solution, and the mixture was cooled under ice cooling. A solution of methyl chloroformate (8.80 mL, 0.114 mol) in 10 mL of ethyl acetate was added dropwise to the cooled mixture over a period of 30 min. The reaction solution was warmed to room temperature followed by stirring for 3 hr. The disappearance of 2-fluoroaniline from the reaction solution was confirmed by high performance liquid chromatography. Thereafter, 20 mL of water was added thereto under ice cooling to stop the reaction. Next, 50 mL of ethyl acetate and 50 mL of water were added to the reaction mixture to carry out extraction. The organic layer was washed with 40 mL of water and 30 mL of a saturated sodium hydrogencarbonate solution and was then dried over an hydrous magnesium sulfate. The solvent was then removed from the organic layer by distillation to give 16.5 g of 2-fluoro-N-methoxycarbonylaniline as a substantially single product (yield 94.4%).

Provenance & Evidence