1-(Bromomethyl)-2,4-difluorobenzene → HCID 19365952, compound

Participants

Reaction Steps

2,4-Difluorobenzyl bromide (9.0 ml, 70 mmol) was added dropwise to a suspension of magnesium (1.8 g, 75 mmol) in diethyl ether (50 ml) under an atmosphere of dry nitrogen at a sufficient rate to maintain a gentle reflux. The resulting solution was stirred for 15 minutes at room temperature and was then added dropwise to a solution of the product of part (i) (10.0 g, 50 mmol) in THF (70 ml) at -70° C. under an atmosphere of nitrogen. The mixture was warmed to room temperature, stirred for 2 hours then quenched with dilute hydrochloric acid (2M, 50 ml). The layers were separated and the aqueous phase was extracted with diethyl ether (2×50 ml). The combined extracts were dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash chromatography on silica by elution with ether/hexane (1:1). The appropriate fractions were combined, evaporated under reduced pressure and the crude product was triturated with diethyl ether to give the title compound as a yellow solid, (10.7 g), m.p. 93°-95° C. Found: C,58.01; H,2.99; N,5.17; C13H8ClF2NO requires: C,58.33; H,3.01; N,5.23%.

Provenance & Evidence