Dimethylformamide → 4-(2,2,2-Trifluoro-1-methyl-1-(trifluoromethyl)ethyl)anisole

HRID 1634353Notes

Reaction equation

HRID 1634353 reaction equation
[F:1][C:2]([F:16])=[C:3]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:4]([F:7])([F:6])[F:5].CI.[F-:19].[Cs+].[CH3:21]N(C=O)C>O>[F:19][C:2]([F:16])([F:1])[C:3]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)([CH3:21])[C:4]([F:5])([F:6])[F:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 25953Cesium fluorideHCID 117763304-(2,2-Difluoro-1-(trifluoromethyl)ethenyl)anisole

Product 1

HCID 186776014-(2,2,2-Trifluoro-1-methyl-1-(trifluoromethyl)ethyl)anisoleYield 10%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of Compound 74 (570 mg, 2.4 mmol), MeI (430 mg, 3.0 mmol), and CsF (760 mg, 5.0 mmol) in DMF (4 ml) was stirred at 80° C. for 3 days. The mixture was diluted with H2O. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined solution was dried (Na2SO4) and concentrated in vacuo to give crude product, which was purified by column chromatography on silica gel to give Compound 75 (70 mg, 10%) as a yellow oil.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with CH2Cl2
  3. dry with materialThe combined solution was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give crude product, which
  6. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-665f97d163074b4a8d115c57072eb292
Source dataset
uspto-grants-2003_01
Patent number
US06506775B1

Reaction notes

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