3-Fluoroacetophenone → 1-(3-Fluorophenyl)-2-(5-trifluoromethyl-2-pyridinyl)ethanone

HRID 354238

反応式

HRID 354238 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[CH3:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=1)=[O:14].[H-].[Na+].[NH4+].[Cl-]>COCCOC>[F:21][C:17]1[CH:16]=[C:15]([C:13](=[O:14])[CH2:12][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=2)[CH:20]=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 99673-FluoroacetophenoneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 923422-Chloro-5-(trifluoromethyl)pyridine

生成物 1

HCID 129887451-(3-Fluorophenyl)-2-(5-trifluoromethyl-2-pyridinyl)ethanone収率 84%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
42.5 °C

実験手順

A reaction vessel was charged with 2-chloro-5-trifluoromethylpyridine (8 g, 44 mmol), 3-fluoroacetophenone (6.4 g, 46 mmol) and DME (56 ml). Sodium hydride (as a 60% oil dispersion, 5.8 g, 145 mmol) was added in portions to the mixture under nitrogen at room temperature. The mixture was stirred at 40-45° C. overnight. Upon the completion of the reaction, aqueous NH4Cl solution (240 ml) was added to the reaction mixture at room temperature. The mixture was stirred for 0.5 hr and filtered. The cake was washed with water, slurried in hexanes (32 ml) and dried in a vacuum oven to give 10.44 g (84%) of the title compound (a mixture of ketone and enol isomers) as a solid with purity 99% AUC by HPLC (Phenomenex Luna 3μ cyano, 100 mm×4.6 mm. Flow rate: 1 ml/min. UV detection: 220 nm. Eluent: 75% A, 25% B. A: 80/20/0.05 water/acetonitrile/TFA. B: 20/80/0.05 water/acetonitrile/TFA ).

後処理

  1. additionwas added to the reaction mixture at room temperature
  2. stirringThe mixture was stirred for 0.5 hr
  3. filtrationfiltered
  4. washThe cake was washed with water
  5. customdried in a vacuum oven

出典と根拠

ORDレコード
ord-52a30f1acfa54175929863fcf3ffd3a6
出典データセット
uspto-grants-2004_06
特許番号
US06756498B2

関連ノート

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