3-(Trifluoromethyl)phenol → 4-(3-Trifluoromethylphenoxy)-2-(4-fluorophenyl)pyrimidine

HRID 651731

반응식

HRID 651731 반응식
Cl[C:2](Cl)=[CH:3][CH:4]=O.C(O)(=O)C.[F:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[NH:17])=[CH:14][CH:13]=1.[F:21][C:22]([F:31])([F:30])[C:23]1[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC>[F:21][C:22]([F:30])([F:31])[C:23]1[CH:24]=[C:25]([CH:26]=[CH:27][CH:28]=1)[O:29][C:2]1[CH:3]=[CH:4][N:18]=[C:16]([C:15]2[CH:19]=[CH:20][C:12]([F:11])=[CH:13][CH:14]=2)[N:17]=1

참가 물질

6

반응물 4

HCID 73763-(Trifluoromethyl)phenolHCID 11430Potassium CarbonateHCID 175543,3-Dichloro-2-propenal2회HCID 447849914-Fluorobenzamidine acetate2회

생성물 1

HCID 98624974-(3-Trifluoromethylphenoxy)-2-(4-fluorophenyl)pyrimidine수율 75.4%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매2회

실험 절차

3,3-Dichloroacrolein (10 mmoles) diluted with dimethoxyethane (35 ml), is slowly added to a mixture consisting of a 4-fluorobenzamidine acetate (10 mmoles), 3-trifluoromethylphenol (11 mmoles), potassium carbonate (40 mmoles) and dimethoxyethane (40 ml), which is stirred under reflux. When the addition of 3,3-dichloroacrolein is completed additional 4-fluorobenzamidine acetate (1 mmoles) is added. The reaction mixture is stirred for 3 hours under reflux and subsequently cooled down to ambient temperature over night and filtered through silica. The organic phase is concentrated in vacuo. The residue was purified by chromatography on Al2O3 (petrol ethers/ethyl acetate: 20/1) to yield 2.52 g (75%) of the pure product having a melting point of 52° C.

후처리

  1. additionis slowly added to a mixture
  2. temperatureunder reflux
  3. additionis added
  4. stirringThe reaction mixture is stirred for 3 hours
  5. temperatureunder reflux
  6. filtrationfiltered through silica
  7. concentrationThe organic phase is concentrated in vacuo
  8. customThe residue was purified by chromatography on Al2O3 (petrol ethers/ethyl acetate: 20/1)

출처 및 근거

ORD 기록
ord-1fa297181fbc4fb997311be60cf04592
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06281358B1

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