Potassium bisulfate → 2-Bromo-4-ethenyl-1-methylbenzene
反応式
OS([O-])(=O)=O.[K+].[Br:7][C:8]1[CH:9]=[C:10]([CH:15](O)[CH3:16])[CH:11]=[CH:12][C:13]=1[CH3:14]>C1(C=CC(O)=CC=1)O>[Br:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=1[CH3:14])[CH:15]=[CH2:16]参加物
4
実験手順
KHSO4 (0.55 g, 34 mmol), hydroquinone (0.142 g, 1.3 mmol), and 1-(3-bromo-4-methyl-phenyl)ethanol (17.2 g, 80 mmol) were added to a 25 mL round-bottom flask equipped with a distillation equipment. Under stirring, the system was vacuumed at 3 mm Hg and heated. A liquid product (13.6 g, 86% yield) was colleted at 102° C. (3 mm Hg). 1H NMR (300 MHz, CDCl3) δ 2.37 (3H, s), 5.23 (1H, d, J=10.9 Hz), 5.69 (1H, d, J=17.6 Hz), 6.60 (1H, dd, J=10.9, 17.6 Hz), 7.16 (1H, d, J=7.8 Hz), 7.21 (1H, d, J=7.8 Hz), 7.57 (1H, s); 13C NMR (75 MHz, CDCl3) δ 22.63, 114.32, 125.04, 125.09, 129.92, 130.76, 135.30, 137.11, 137.22 ppm; IR (neat) 3091 (m), 3063 (m), 3016 (s), 2985 (s), 2964 (m), 1899 (w), 1833 (w), 1701 (w), 1629 (m), 1602 (m), 1554 (s), 1492 (s), 1450 (s), 1380 (s), 1304 (w), 1278 (m), 1205 (m), 1037 (s), 989 (s), 914 (s), 833 (s), 854 (s), 826 (s) cm−1; MS m/z 197(M++1) 171, 169, 117, 115, 91, 89; HRMS calcd.: C9H9Br 195.9888, found: 195.9887.