Allyl bromide → 1-((S)-1-allyloxy-ethyl)-4-fluoro-benzene

참여 물질

반응 단계

To a stirred suspension of sodium hydride (3.14 g, 55% dispersion in oil) in dry DMF (180 ml) under an argon atmosphere was added (S)-1-(4-fluorophenyl)-ethanol (8.41 g, CAS 101219-73-2). Allyl bromide (6.6 ml) was then added dropwise. The reaction mixture was stirred for 30 min at room temperature and was then quenched by addition of water. The mixture was extracted with ethyl acetate twice. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give 1-((S)-1-allyloxy-ethyl)-4-fluoro-benzene (8.66 g, 80%) as a colourless liquid. 1H NMR (300 MHz, CDCl3, δ ppm): 1.43 (d, J=6.6 Hz, 3H), 3.84 (m, 2H), 4.45 (q, J=6.6 Hz, 1H), 5.15 (dd, J1=10.5 Hz, J2=1.8 Hz, 1H), 5.22 (dd, J1=17.4 Hz, J2=1.8 Hz, 1H), 5.89 (m, 1H), 7.03 (m, 2H), 7.29 (m, 2H).

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