Allyl bromide → HCID 58018656, compound

Participants

Reaction Steps

A mixture of 1-(4-fluoro-2-hydroxyphenyl)ethanone (7.50 g, 48.7 mmol), 3-bromoprop-1-ene (6.48 g, 53.5 mmol), and potassium carbonate (13.5 g, 97.0 mmol) in DMF (75 mL) was vigorously stirred at rt for 24 h. The reaction mixture was diluted with water (100 mL) while stirring. The white precipitate was collected by vacuum filtration. The solid was rinsed with water (300 mL). The solid was dried under high vacuum to afford 1-(2-(allyloxy)-4-fluorophenyl)ethanone (7.92 g, 40.0 mmol, 82% yield) as a white solid. LCMS (M+Na)+=217.1. 1H NMR (500 MHz, chloroform-d) δ 7.82 (dd, J=8.7, 7.0 Hz, 1H), 6.71 (ddd, J=8.7, 7.6, 2.3 Hz, 1H), 6.66 (dd, J=10.8, 2.3 Hz, 1H), 6.08 (ddt, J=17.3, 10.6, 5.3 Hz, 1H), 5.55-5.41 (m, 1H), 5.41-5.29 (m, 1H), 4.63 (dt, J=5.4, 1.4 Hz, 2H), 2.62 (s, 3H).

Provenance & Evidence