Thionyl Chloride → HCID 118308888, compound

Participants

Reaction Steps

(2-(But-3-en-1-yloxy)-5-fluorophenyl)methanol (6.3 g, 32.1 mmol, 1 equiv) was taken up in thionyl chloride (107 mL) and heated to reflux for 1 h. Upon cooling to ambient temperature, the solution was concentrated in vacuo. The residue was concentrated in vacuo with benzene (×3) to remove residual thionyl chloride and provide the benzyl chloride (6.3 g, 91%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.12 (dd, J=8.7, 3.1 Hz, 1H), 6.98 (ddd, J=8.9, 8.0, 3.1 Hz, 1H), 6.82 (dd, J=9.0, 4.3 Hz, 1H), 5.93 (ddt, J=17.1, 10.3, 6.8 Hz, 1H), 5.25-5.09 (m, 2H), 4.62 (s, 2H), 4.05 (t, J=6.5 Hz, 2H), 2.58 (qt, J=6.6, 1.3 Hz, 2H).

Provenance & Evidence