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

HRID 651728

반응식

HRID 651728 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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 acetonitrile (35 ml), which is stirred under reflux. 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.

후처리

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

출처 및 근거

ORD 기록
ord-e641c6794df94fafba17e5482fd781e1
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06281358B1

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