Ethanol → Ethyl 2-bromo-4-fluorobenzoate

Participants

Reaction Steps

281 mg (2.21 mmol) of oxalyl chloride are added to a solution of 220 mg (1.01 mmol) of 2-bromo-4-fluorobenzoic acid in 5 ml of absolute toluene under argon, and the mixture is stirred at RT for 4 hours. The solvent is removed in vacuo, and the residue is taken up three times in DCM and the solvent is removed each time in vacuo. A yellow oil is obtained and is dissolved in a little DCM. 213 mg (2.10 mmol) of triethylamine and 2 ml of ethanol are added to the solution, and the mixture is stirred at RT for three hours. The reaction mixture is diluted with twice the volume of distilled water and extracted with DCM. The solvent of the organic phase is removed in vacuo, and the residue is chromatographed on silica gel (eluent: DCM/methanol 20:1). 100 mg (39% of theory) of the product are obtained.

Provenance & Evidence