Water → 1,2-Bis-benzyloxy-3-bromo-5-trifluoromethyl-benzene

HRID 2251607Notes

Reaction equation

HRID 2251607 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([OH:12])[C:3]=1O.[C:14]([O-:17])([O-])=O.[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CC(C)=O.CCOC(C)=O>[CH2:20]([O:12][C:4]1[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=[C:2]([Br:1])[C:3]=1[O:17][CH2:14][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 596430371,2-Benzenediol, 3-bromo-5-(trifluoromethyl)-

Product 1

HCID 596430241,2-Bis-benzyloxy-3-bromo-5-trifluoromethyl-benzene

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-bromo-5-trifluoromethyl-benzene-1,2-diol (510 mg, 1.98 mmol) in 10 mL acetone, K2CO3 (2.74 g, 19.84 mmol, 10 eq.) and benzyl bromide (1.02 g, 5.95 mmol, 3 eq.) were added and the solution was refluxed for 4 h. After cooling to r.t., H2O and EtOAc were added to the mixture and the phases were separated The organic fraction was washed with saturated NaCl solution, dried over MgSO4 and evaporated in vacuo. The crude product was purified using flash chromatography (silica gel, hexane/EtOAc 10:1) to yield the title compound as a colorless solid.

Workup

  1. temperaturethe solution was refluxed for 4 h
  2. customthe phases were separated The organic fraction
  3. washwas washed with saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-358d3336000e4671bd5237234139eec0
Source dataset
uspto-grants-2008_01
Patent number
US07319101B2

Reaction notes

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