Dimethylformamide → Allyl 4-(2,2,2-trifluoroethoxy)phenyl ether

HRID 51083Notes

Reaction equation

HRID 51083 reaction equation
CN(C=O)C.[F:6][C:7]([F:18])([F:17])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.[CH2:19](Br)[CH:20]=[CH2:21].C(=O)([O-])[O-].[Cs+].[Cs+]>CCOC(C)=O.O>[F:6][C:7]([F:17])([F:18])[CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:21][CH:20]=[CH2:19])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 130853484-(2,2,2-Trifluoroethoxy)phenol

Product 1

HCID 22737359Allyl 4-(2,2,2-trifluoroethoxy)phenyl ether

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a DMF 30 ml solution of 4-(2,2,2-trifluoroethoxy)phenol (2.6 g, 13.6 mmol) and allyl bromide (3.53 ml, 40.8 mmol) was added cesium carbonate (4.85 g, 14.9 mmol). This suspension was heated to 60° C. for 18 hr, diluted with AcOEt and water. The organic layer was separated, and the aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on silica gel eluting with 10% AcOEt/hexanes to give the title compound.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted twice with AcOEt
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed on silica gel eluting with 10% AcOEt/hexanes

Sources & evidence

ORD record
ord-81c4dd6492d843df979e205d9c209289
Source dataset
uspto-grants-2004_03
Patent number
US06713508B2

Reaction notes

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