Diethyl Ether → 1-(Benzyloxy)-2-bromo-4-(trifluoromethyl)benzene

HRID 269531Notes

Reaction equation

HRID 269531 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1[OH:8].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)C>CC(C)=O.O>[CH2:13]([O:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]([F:10])([F:11])[F:12])=[CH:3][C:2]=1[Br:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27611682-Bromo-4-(trifluoromethyl)phenol

Product 1

HCID 187826691-(Benzyloxy)-2-bromo-4-(trifluoromethyl)benzeneYield 85%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 3-bromo-4-hydroxybenzotrifluoride (6.03 g, 25 mmol) in acetone (1000 ml) was treated with benzyl bromide (4.67 g, 3.25 ml, 27.5 mmol) and potassium carbonate (5.18 g, 37.5 mmol). The mixture was stirred and heated to reflux under nitrogen for 2 h. After cooling, diethyl ether (300 ml) and water (300 ml) were added and the aqueous phase re-extracted with diethyl ether (100 ml). The combined organic layers were washed with water, dried (MgSO4) and the solvent removed in vacuo. The orange oil was flash chromatographed (silica gel, 2-5% dichloromethane-isohexane) to give the title compound as a clear oil (7.0 g, 85%).

Workup

  1. temperatureheated
  2. temperatureto reflux under nitrogen for 2 h
  3. temperatureAfter cooling
  4. extractionthe aqueous phase re-extracted with diethyl ether (100 ml)
  5. washThe combined organic layers were washed with water
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo
  8. customchromatographed (silica gel, 2-5% dichloromethane-isohexane)

Sources & evidence

ORD record
ord-b3c7d4e19f464c9d9bd9ce4f7a4b83aa
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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