Water → 2-Benzyloxy-5-(trifluoromethoxy)benzene

HRID 2288713Notes

Reaction equation

HRID 2288713 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]([F:20])([F:19])[O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:1]([O:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:10]([F:9])([F:19])[F:20])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 70015p-(Trifluoromethoxy)phenol

Product 1

HCID 215840942-Benzyloxy-5-(trifluoromethoxy)benzeneYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (66.17 ml, 95.35 g, 0.56 mol) was added to a mixture of 4-(trifluoromethoxy)phenol (90.26 g, 0.51 mol) and potassium carbonate (140.97 g, 1.2 mol) in dimethylformamide (160 ml) and the mixture was stirred at room temperature for 72 hours. The mixture was poured into water (1.5 l) and extracted with ethyl acetate (3×500 ml). The combined organic fractions were washed with aqueous sodium carbonate (saturated, 500 ml), dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colorless solid (133.5 g, 99%). 1H NMR (360 MHz, CDCl3) d 7.39 (5H, m), 7.14 (2H, d, J=9.0 Hz), 6.95 (2H, d, J=9.0 Hz), and 5.05 (2H, s).

Workup

  1. extractionextracted with ethyl acetate (3×500 ml)
  2. washThe combined organic fractions were washed with aqueous sodium carbonate (saturated, 500 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2e27634cadcc4fc197cc351789a04c92
Source dataset
uspto-grants-2000_07
Patent number
US06090819

Reaction notes

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