Thionyl Chloride → 2-(Chloromethyl)-4-fluoro-1-methoxybenzene

Participants

Reaction Conditions

Reaction Steps

Neat (5-Fluoro-2-methoxy-phenyl)-methanol (19.587 g, 1 equiv.) was added to neat SOCl2 (42.2 mL, 4.6 equiv.) at −78° C. under a nitrogen atmosphere and the solution was then allowed to warn to room temperature and stirred until evolution of gas had ceased. An equivalent volume of anhydrous toluene was added to the flask and the solution heated to 60° C. On cooling the reaction solution was poured onto ice water. The toluene layer was separated and dried (MgSO4) and the solvent removed under reduced pressure. The crude material was sublimed (60-80° C./0.05 mBarr) to give the title compound as a white solid (13.40 g, 61%). 1H NMR (300 MHz, CDCl3): δ 3.87 (s, 3H), 4.60 (s, 2H), 6.79-7.20 (m, 3H).

Provenance & Evidence