N-bromobutanimide → [2-Bromo-3,5-bis(methoxymethoxy)phenyl]methanol

반응식

[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH2:15][OH:16])[CH:8]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:10]=1.C1C(=O)N([Br:24])C(=O)C1>CN(C=O)C.C(OCC)(=O)C>[Br:24][C:6]1[C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:10][C:9]([O:11][CH2:12][O:13][CH3:14])=[CH:8][C:7]=1[CH2:15][OH:16]

참가 물질

실험 절차

A solution of (3,5-bis-methoxymethoxy-phenyl)-methanol (9.16 g, 40.2 mmol) in DMF (40 mL) was treated with NBS (7.51 g, 42.2 mmol) at room temperature and the mixture was stirred at same temperature for 30 min. The residue was diluted with ethyl acetate and washed with brine. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=1:1) to afford the title compound (10.2 g, 83%). 1H NMR (300 MHz, CDCl3) δ 6.91 (s, 1H), 6.81 (s, 1H), 5.24 (s, 2H), 5.17 (s, 2H), 4.72 (d, J=6.3 Hz, 2H), 3.52 (s, 3H), 3.47 (s, 3H), 2.05 (t, 1H).