Hydrochloric Acid → 2-Trifluoromethyl-4-(4-ethoxyphenoxy)-1-benzyloxybenzene

HRID 1940257Notes

Reaction equation

HRID 1940257 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=1.[CH2:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)[CH3:21].C(=O)([O-])[O-].[K+].[K+].Cl>[Cu]>[F:17][C:16]([F:19])([F:18])[C:4]1[CH:3]=[C:2]([O:29][C:26]2[CH:27]=[CH:28][C:23]([O:22][CH2:20][CH3:21])=[CH:24][CH:25]=2)[CH:7]=[CH:6][C:5]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 121504-EthoxyphenolHCID 186201601-(Benzyloxy)-4-bromo-2-(trifluoromethyl)benzene

Product 1

HCID 214662732-Trifluoromethyl-4-(4-ethoxyphenoxy)-1-benzyloxybenzeneYield 41.8%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

Then, 5.10 g of 4-bromo-2-trifluoromethyl-1-benzyloxybenzene, 2.34 g of p-ethoxyphenol, 2.13 g of potassium carbonate, 100 mg of copper and 200 mg of cuprous chloride were charged into a reaction vessel, and stirred at 130° C. to 140° C. for 5 hours. The reaction solution was cooled to room temperature, poured into ice-water and then acidified by adding 10% hydrochloric acid. The solution was extracted twice with 100 ml of diethyl ether. Then, the ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to give a crude product. This crude product was subjected to silica gel chromatography to give 2.50 g of 2-trifluoromethyl-4-(4-ethoxyphenoxy)-1-benzyloxybenzene, (yield, 41%).

Workup

  1. extractionThe solution was extracted twice with 100 ml of diethyl ether
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give a crude product
  6. customto give

Sources & evidence

ORD record
ord-1ce61016b8cc4b16a0ccb7b2956c3b6e
Source dataset
uspto-grants-1997_12
Patent number
US05698702

Reaction notes

Loading…