Potassium bisulfate → 2-Bromo-4-ethenyl-1-methylbenzene

HRID 1242821Notes

Reaction equation

HRID 1242821 reaction equation
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]

Participants

4

Reactant 2

HCID 516920Potassium bisulfateHCID 219403321-(3-Bromo-4-methylphenyl)ethan-1-ol

Product 1

HCID 219403312-Bromo-4-ethenyl-1-methylbenzeneYield 86.3%

Reagents, catalysts & solvents 1

HCID 785HydroquinoneCatalyst

Procedure

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.

Workup

  1. customequipped with a distillation equipment
  2. temperatureheated

Sources & evidence

ORD record
ord-50644db5622d4545a02b8533e63a1ecc
Source dataset
uspto-grants-2006_10
Patent number
US07115762B2

Reaction notes

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