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

HRID 411827

反応式

HRID 411827 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 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.

後処理

  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)

出典と根拠

ORDレコード
ord-a0b0745c9fb7486b9339e07a4d005f05
出典データセット
uspto-grants-2003_05
特許番号
US06559307B2

関連ノート

読み込み中…