Benzyl Chloride → 1-(Benzyloxy)-4-bromo-2-(trifluoromethyl)benzene

HRID 1940256Notes

Reaction equation

HRID 1940256 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:4]([C:9]([F:10])([F:11])[F:12])[CH:3]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 142784o-Cresol, 4-bromo-alpha,alpha,alpha-trifluoro-

Product 1

HCID 186201601-(Benzyloxy)-4-bromo-2-(trifluoromethyl)benzeneYield 80.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Then, 8.47 g of 4-bromo-2-trifluoromethylphenol, 5.34 g of potassium carbonate, 4.49 g of benzyl chloride and 100 ml of N,N-dimethylformamide were charged into a reaction vessel, and stirred under ice cooling. After 24 hours, the reaction solution was poured into ice-water and extracted three times with 50 ml of diethyl ether. The ether layers were combined, washed with an aqueous 10 % sodium hydroxide solution, dried over anhydrous magnesium sulfate and then concentrated to give a crude product. This crude product was subjected to silica gel chromatography to give 9.38 g of 4-bromo-2-trifluoromethyl-1-benzyloxybenzene, (yield, 81%).

Workup

  1. extractionextracted three times with 50 ml of diethyl ether
  2. washwashed with an aqueous 10 % sodium hydroxide solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give a crude product
  6. customto give

Sources & evidence

ORD record
ord-57667d81d75d4a31b924bd2f9fa21b43
Source dataset
uspto-grants-1997_12
Patent number
US05698702

Reaction notes

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