Phenol → 2-Phenoxy-4-(trifluoromethyl)pyrimidine

HRID 2070119Notes

Reaction equation

HRID 2070119 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:18]([C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidine

Product 1

HCID 538928452-Phenoxy-4-(trifluoromethyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-chloro-4-trifluoromethylpyrimidine (3.0 g, 0.016 mol) in DMF (30 ml) were successively added phenol (1.9 g, 20 mmol), potassium carbonate (3.3 g, 24 mmol) and Cu(I) (100 mg). The reaction mixture was stirred for 7 h at 90° C. The resulting reaction mixture was partitioned between MTBE and water. The aqueous layer was extracted with MTBE. The solvent was removed from the organic layers in vacuo. 2-Phenoxy-4-trifluoromethylpyrimidine was obtained as a yellowish solid (3.0 g). 1H-NMR (CDCl3): δ=7.2-7.5 (m, 6H); 8.7 ppm (m, 1H).

Workup

  1. customThe resulting reaction mixture
  2. customwas partitioned between MTBE and water
  3. extractionThe aqueous layer was extracted with MTBE
  4. customThe solvent was removed from the organic layers in vacuo

Sources & evidence

ORD record
ord-5c47358cd8cf46fbb145178c509927ed
Source dataset
uspto-grants-2012_10
Patent number
US08299262B2

Reaction notes

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