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

HRID 651728

反応式

HRID 651728 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e641c6794df94fafba17e5482fd781e1
出典データセット
uspto-grants-2001_08
特許番号
US06281358B1

関連ノート

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