Potassium bisulfate → 2-Bromo-4-ethenyl-1-methylbenzene
반응식
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]참가 물질
4
실험 절차
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.