Cesium fluoride → 1-(Benzyloxy)-2-chloro-4-(3,3,3-trifluoroprop-1-en-1-yl)benzene

HRID 2113160Notes

Reaction equation

HRID 2113160 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[Cl:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)S([O-])(=O)=O.[F:26][C:27]([F:49])([F:48])[CH2:28][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[Cl:17][C:10]1[CH:11]=[C:12]([CH:13]=[CH:28][C:27]([F:49])([F:48])[F:26])[CH:15]=[CH:16][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 27354954-(Benzyloxy)-3-chlorobenzaldehydeHCID 11179430Triphenyl(2,2,2-trifluoroethyl)phosphanium trifluoromethanesulfonate

Product 1

HCID 690498881-(Benzyloxy)-2-chloro-4-(3,3,3-trifluoroprop-1-en-1-yl)benzene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-benzyloxy-3-chlorobenzaldehyde (0.25 g, 2.0 mmol), 2,2,2-trifluoroethyltriphenylphosphonium trifluoromethanesulfonate (0.49 g, 1.0 mmol) and CsF (0.76 g, 5.0 mmol) in DMF (10 mL) was stirred at 25° C. for 16 h. The reaction was then diluted with ethyl acetate, washed with water and dried. Removal of the solvent gave a residue which was purified by preparative TLC to give 1-(3-chloro-4-benzyloxyphenyl)-3,3,3-trifluoropropene. This product (65 mg, 0.2 mmol) was dissolved in ethyl acetate (2 mL) and hydrogenated (1 atm) in the presence of 10% palladium on carbon for 1 hr. Removal of the catalyst and solvent give 2-chloro-4 (3,3,3-trifluoropropyl)phenol as an oil.

Workup

  1. washwashed with water
  2. customdried
  3. customRemoval of the solvent
  4. customgave a residue which
  5. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-f0b2be626af740b89acb6b47a7ed7052
Source dataset
uspto-grants-2009_04
Patent number
US07524882B2

Reaction notes

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