Dimethylformamide → 1-Bromo-2-(2,2,2-trifluoroethoxy)benzene

HRID 2101201Notes

Reaction equation

HRID 2101201 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[F:9][C:10]([F:14])([F:13])[CH2:11]I.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:9][C:10]([F:14])([F:13])[CH2:11][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethane

Product 1

HCID 226154791-Bromo-2-(2,2,2-trifluoroethoxy)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.35 g (2 mmol) of 2-bromophenol, 0.63 g (3 mmol) of 2,2,2-trifluoroethyliodide, 0.55 g (4 mmol) of potassium carbonate in 2 Ml of DMF was reacted at 150° C. in a microwave system (Personal Chemistry, Smithcreator) for 30 min. After cooling to RT, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic fraction was dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (5%, 10% successively EtOAc:hexanes) to give the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic fraction was dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography (5%, 10% successively EtOAc

Sources & evidence

ORD record
ord-2cdb01bfd46944a6a1e50249a8fc2372
Source dataset
uspto-grants-2009_08
Patent number
US07572822B2

Reaction notes

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