2,2,2-Trifluoroethanol → HCID 60098084, compound

HRID 2070349Notes

Reaction equation

HRID 2070349 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[CH:5]=[CH:6][C:7]=1F.[F:12][C:13]([F:17])([F:16])[CH2:14][OH:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=1[O:15][CH2:14][C:13]([F:17])([F:16])[F:12]

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 11430Potassium CarbonateHCID 696992-Bromo-1-fluoro-4-nitrobenzene

Product 1

HCID 60098084HCID 60098084, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

3-Bromo-4-fluoronitrobenzene (1.0 eq) was added to a stirring solution of 2,2,2-trifluoroethanol (1.1 eq) and potassium carbonate (2.0 eq) in DMF. The solution was heated for 18 hours at 90° C. at which time no starting material was apparent by LCMS. The solution was cooled and filtered through Celite and the plug washed with EtOAc. The organic layer is then washed with brine and water, dried over MgSO4, filtered and concentrated to yield the desired product 97% pure, 80% yield. LC Rt=2.975 min. MH+=302.0

Workup

  1. temperatureThe solution was cooled
  2. filtrationfiltered through Celite
  3. washthe plug washed with EtOAc
  4. washThe organic layer is then washed with brine and water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7ee6f5ef961140b7ba551753603b1084
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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