Dimethylformamide → HCID 66891080, compound

Participants

Reaction Steps

A THF (25 mL) solution of {5-fluoro-2-(methyloxy)-3-[(phenylmethyl)oxy]phenyl}methanol (6.94 g, 26 mmol) was cooled to 0° C. and was then treated with thionyl chloride (2.5 mL, 34 mmol) and DMF (5.0 mL, 65 mmol) for 30 min. Ethyl acetate and ice water were then added. The layers were partitioned, and the aqueous phase was extracted with ethyl acetate. The organic extracts were combined, dried over magnesium sulfate, filtered, and concentrated in vacuo. The product, 1-(chloromethyl)-5-fluoro-2-(methyloxy)-3-[(phenylmethyl)oxy]benzene, was obtained as an orange oil (6.82 g, 24.3 mmol, 93% yield), which solidified upon storage in the freezer. 1H NMR (400 MHz, CDCl3): δ 7.45-7.26 (m, 5H), 6.72-6.66 (m, 2H), 5.09 (s, 2H), 4.61 (s, 2H), 3.91 (s, 3H).

Provenance & Evidence