Hexane → 2-Bromo-1-(3,4-dichlorophenyl)propan-1-one

Participants

Reaction Steps

To a solution of 3′,4′-dichloropropiophenone (81, 5.02 g, 0.247 mol) in CH2Cl2 (100 mL) was added ten drops of bromine. After stirring at room temperature under nitrogen for several min, the characteristic red color of bromine disappeared indicating initiation of the reaction. The remainder of the bromine (1.27 mL, 24.7 mmol) was added dropwise and the reaction solution was allowed to stir at room temperature under nitrogen atmosphere for 1.75 h. Analysis by TLC (silica, 2:1 hexane:CH2Cl2) indicated consumption of starting material. The reaction solution was quenched and brought to a pH of 9 with a saturated aqueous solution of NaHCO3 and concentrated NH4OH. The solution was extracted with CH2Cl2, dried (Na2SO4), filtered, concentrated, and dried to give 7.14 g (100%) of 2-bromo-(3′,4′-dichlorophenyl)propan-1-one as a white solid. Characterization data is similar with data reported in Anderson, W. K.; Jones, A. N., J. Med. Chem. 1984, 27, (12), 1559-1565.

Provenance & Evidence