Thionyl Chloride → 13923-56-3

Participants

Reaction Steps

To ethyl [4-bromo-2-(hydroxymethyl)phenoxy]acetate (Example 7, 5.00 g, 17.4 mmol) in 150 mL CH2Cl2 under Ar, was added SOCl2 (4.13 g, 34.7 mmol) dropwise with stirring. The mixture was then heated to reflux for 4 hours, cooled, and the volatiles were removed under reduced pressure. The crude oil was then subjected to flash chromatography (15% EtOAc/hexanes) to provide 4.02 g (76%) of the desired product as a clear oil. 1H-NMR (acetone-d6, δ): 1.25 (t, 3H), 3.50 (ddd, 2H), 4.22 (q, 2H), 5.37 (dd, 1H), 6.77 (d, 1H), 7.29 (m, 1H), 7.37 (m, 1H); LRMS (GC/MS/EI) 270 [M]+.

Provenance & Evidence