Phosphorus tribromide → 2-(Bromomethyl)-1-fluoro-4-iodobenzene

Participants

Reaction Steps

Phosphorus tribromide 1.0 M soln. in DCM (18.9 mL, 18.9 mmol) was added dropwise to a 0° C. solution of (2-fluoro-5-iodo-phenyl)-methanol G-6 (9.52 g, 37.8 mmol) in DCM (215 mL) and the resulting mixture was stirred for 1 h before being quenched with water. The layers were separated and the aqueous phase was re-extracted with DCM (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo to give the crude product that was purified by flash chromatography (eluting with 5% EtOAc in hexane) to give the title compound as a white solid. LC-MS B: tR=0.92 min; No ionisation; 1H NMR (DMSO) δH: 7.93 (dd, J1=7.1 Hz, J2=2.3 Hz, 1H), 7.74 (ddd, J1=8.6 Hz, J2=4.9 Hz, J3=2.3 Hz, 1H), 7.10 (dd, J1=10.0 Hz, J2=8.7 Hz, 1H), 4.66 (s, 2H).

Provenance & Evidence