Potassium Carbonate → 1-Bromo-4-fluoro-2-(2,2,2-trifluoroethoxy)benzene

HRID 1051858Notes

Reaction equation

HRID 1051858 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[CH2:22][C:23]([F:26])([F:25])[F:24])(=O)=O>C(#N)C.CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH2:22][C:23]([F:26])([F:25])[F:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 27246002-Bromo-5-fluorophenol

Product 1

HCID 579845111-Bromo-4-fluoro-2-(2,2,2-trifluoroethoxy)benzeneYield 186.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

To a stirred solution of 2-bromo-5-fluorophenol (1.5 g) in acetonitrile (0.5 mL) and DMF (8.5 mL) in a microwave tube was added potassium carbonate (2.1 g) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (2.37 g). The mixture was heated to 150° C. in a microwave oven for 30 minutes. In a second microwave tube the same reaction was repeated. Both mixtures were combined. The solvent was removed in vacuum, ethyl acetate and hexane (1:1) was added and the mixture was washed with water. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 4.0 g of the title compound.

Workup

  1. customIn a second microwave tube the same reaction
  2. customThe solvent was removed in vacuum, ethyl acetate and hexane (1:1)
  3. additionwas added
  4. washthe mixture was washed with water
  5. washThe organic phase was washed with saturated sodium chloride solution
  6. dry with materialdried (sodium sulfate)
  7. customthe solvent was removed in vacuum

Sources & evidence

ORD record
ord-c5d7022493094e1dab4b1fb2306e777e
Source dataset
uspto-grants-2016_07
Patent number
US09388177B2

Reaction notes

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