Potassium Hydroxide → 2-bromo-6-nitrobenzyl (2E)-but-2-en-1-yl ether

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Reaction Steps

To a solution of KOH (0.57 g, 0.099 mol) in (2E)-but-2-en-1-ol (100 mL) was added 1-bromo-2-(bromomethyl)-3-nitrobenzene (10 g, 0.033 mol), and the mixture was stirred at r.t for 30 min. Then the mixture was washed with water (200 mL*4), extracted with EtOAc, dried over Na2SO4, concentrated in vacuo. The residue was purified via chromatography (petrol ether) to give 2-bromo-6-nitrobenzyl (2E)-but-2-en-1-yl ether. 1H-NMR (400 MHz, CDCl3) δ 7.76 (d, J=8.0 Hz, 1H), 7.75 (d, J=8.0 Hz, 1H), 7.25˜7.30 (m, 1H), 5.68˜5.77 (m, 1H), 5.51˜5.58 (m, 1H), 4.82 (s, 2H), 1.69 (d, J=6.0 Hz, 3H).

Provenance & Evidence