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

HRID 411830

反応式

HRID 411830 の反応式
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

参加物

6

反応物 4

HCID 73763-(Trifluoromethyl)phenolHCID 11430Potassium CarbonateHCID 175543,3-Dichloro-2-propenal2 回HCID 447849914-Fluorobenzamidine acetate2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

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) nd 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.

後処理

  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)

出典と根拠

ORDレコード
ord-e7c4df2732b2437d9a887a4aae508376
出典データセット
uspto-grants-2003_05
特許番号
US06559307B2

関連ノート

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