3-(Trifluoromethyl)phenol → 4-(3-Trifluoromethylphenoxy)-2-(4-Trifluoromethylphenyl)-Pyrimidine

HRID 411827

Reaction equation

HRID 411827 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.Cl[C:13](Cl)=[CH:14][CH:15]=O.C([O-])(=O)C.[F:22][C:23]([F:34])([F:33])[C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH2:30])=[NH2+:29])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][C:15]1[CH:14]=[CH:13][N:30]=[C:28]([C:27]2[CH:26]=[CH:25][C:24]([C:23]([F:22])([F:33])[F:34])=[CH:32][CH:31]=2)[N:29]=1

Participants

6

Reactant 4

HCID 73763-(Trifluoromethyl)phenolHCID 10340Sodium CarbonateHCID 175543,3-Dichloro-2-propenalHCID 185417004-Trifluoromethylbenzamidinium acetate

Product 1

HCID 99299504-(3-Trifluoromethylphenoxy)-2-(4-Trifluoromethylphenyl)-PyrimidineYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Trifluoromethylphenol (5 mmoles) and subsequently 3,3-dichloroacrolein (5 mmoles) are added to a mixture consisting of a 4-trifluoromethylbenzamidinium acetate (5 mmoles), sodium carbonate (40 mmoles) and acetonitril (35 ml), which is stirred under reilux. The reaction mixture is stirred for 20 hours under reflux and subsequently cooled down to ambient temperature and filtered through silica. The organic phase is washed with ethyl acetate and concentrated in vacuo. The residue is purified by chromatography on Al2O3 (petrol ethers/ethyl acetate: 2/1) to yield 1.1 g (60%) of the pure product having a melting point of 66-67° C.

Workup

  1. stirringThe reaction mixture is stirred for 20 hours
  2. temperatureunder reflux
  3. filtrationfiltered through silica
  4. washThe organic phase is washed with ethyl acetate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by chromatography on Al2O3 (petrol ethers/ethyl acetate: 2/1)

Sources & evidence

ORD record
ord-a0b0745c9fb7486b9339e07a4d005f05
Source dataset
uspto-grants-2003_05
Patent number
US06559307B2

Linked notes

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