Acetic Acid → 5-Bromo-2-fluorobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 79.5 g (0.296 mol) of 4-bromo-2-bromomethyl-1-fluorobenzene (prepared according to G. E. Stokker, A. W. Alberts et al., J. Med. Chem., 1986, 29, 170), 126 ml of acetic acid, 82.7 g (0.59 mol) of hexamethylenetetramine and 126 ml of water is heated for 2 hours at reflux. The mixture is cooled to 90° C., 99.5 ml of concentrated hydrochloric acid are added and the mixture is heated for 30 min at reflux. Cooling, extraction with ether, washing with water, washing with an aqueous NaHCO3 solution, washing with water, drying over Na2SO4, filtration and evaporation under vacuum are carried out. The residue is purified by chromatography on silica (eluent: 10/1 hexane/ethyl acetate). Yd.: 23.6 g (39%)

Provenance & Evidence