4-Bromophenol → 1-Bromo-4-[(2-methylprop-2-en-1-yl)oxy]benzene

HRID 2194553Notes

Reaction equation

HRID 2194553 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:16][C:17]([CH3:19])=[CH2:18]>CC(C)=O.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:18][C:17]([CH3:19])=[CH2:16])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 3577853-Bromo-2-methyl-1-propene

Product 1

HCID 2359951-Bromo-4-[(2-methylprop-2-en-1-yl)oxy]benzeneYield 93%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo phenol (7.0 g, 40.40 mmol) in acetone (165 mL) was added K2CO3 (27.8 g, 202 mmol) followed by 3-bromo-2-methylprop-1-ene (4.9 mL, 44.5 mmol). The mixture was stirred at reflux temperature for 16 h. After cooling to room temperature, the reaction mixture was diluted with CH2Cl2 (200 mL), washed with H2O (2×50 mL) and brine (50 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title compound (6) (8.0 g, 93%) as a colorless liquid. 1H NMR (CDCl3, 400 MHz) δ 7.37 (d, J=9.2 Hz, 2H), 6.81 (d, J=9.2 Hz, 2H), 5.08 (s, 1H), 5.00 (s, 1H), 4.41 (s, 2H), 1.83 (s, 3H); MS (ESI, M+H+) C10H12BrO, calcd. 227.1. found 227.0, 229.0.

Workup

  1. temperatureat reflux temperature for 16 h
  2. washwashed with H2O (2×50 mL) and brine (50 mL)
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-07ebce91b6ba40f490ed73ab0dd6de96
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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