tert-Butyl methyl ether → 4-Bromo-2-(2-methylallyl)phenol

HRID 2194554Notes

Reaction equation

HRID 2194554 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]CC(C)=C)=[CH:4][CH:3]=1.[C:13](OC)([CH3:16])([CH3:15])[CH3:14]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[C:6]([CH2:15][C:13]([CH3:16])=[CH2:14])[CH:7]=1

Participants

4

Reactant 2

HCID 15413tert-Butyl methyl etherHCID 2359951-Bromo-4-[(2-methylprop-2-en-1-yl)oxy]benzene

Product 1

HCID 867617244-Bromo-2-(2-methylallyl)phenolYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-bromo-4-(2-methylallyloxy)benzene (6) (1.0 g, 4.4 mmol) in DMF (8 mL) was heated in a microwave reactor at 190° C. for 2 h. After cooling to room temperature, the reaction mixture was diluted with methyl tert-butyl ether (50 mL), and washed with H2O (25 mL), brine (25 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, eluting with 5% ethyl acetate in hexanes) to give the title compound (7) (0.7 g, 65%) as a liquid. 1H NMR (CDCl3, 400 MHz) δ 7.27-7.25 (m, 2H), 6.72 (d, J=8.4 Hz, 1H), 4.95 (s, 1H), 4.86 (s, 1H), 3.34 (s, 2H), 1.74 (s, 3H); MS (ESI, M+H+) C10H12BrO, calcd. 227.1. found 227.0, 229.0.

Workup

  1. washwashed with H2O (25 mL), brine (25 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (silica gel, eluting with 5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6395a0d0876e4fa5bf37d43d831eb54b
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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