4-Bromo-2-methylbut-1-ene → HCID 117664395, compound

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Reaction Steps

Dissolve compound 7 (5 g, 0.0176 mol) in 50 ml ether, add sodium metal (0.43 g, 0.0184 mol) into the solution, stir at room temperature for 4 h, then add in isopentenyl bromide (3.2 g, 0.0211 mol), reflux to react for 4 h, stop the reaction. Wash the reaction solution successively with water and saturated brine, separate the organic layer. Desiccate the organic layer over anhydrous magnesium sulfate, filter the solution and remove the solvent by rotary evaporation to obtain a yellow oil which is then feeded to silica gel column chromatography and evaporate the solvent in the eluent to obtain 3.8 g white solid (61%). 1H-NMR (400M, CDCl3) δ (ppm): 1.61 (s, 3H), 1.71 (s, 3H), 34 (d, J=6.8 Hz, 2H), 3.91 (s, 3H), 3.94 (s, 3H), 5.12 (t, J=6.8 Hz, 1H), 6.78 (s, 1H), 7.00 (d, J=16 Hz, 1H), 7.27 (t, J=7.2 Hz, 1H), 7.38 (t, J=7.2 Hz, 2H), 7.52 (d, J=7.2 Hz, 2H), 7.84 (d, J=16 Hz, 1H), 11.66 (s, 1H).

Provenance & Evidence