Methyl Acrylate → (E)-Methyl 3-(4-chloro-2-(trifluoromethyl)phenyl)acrylate

HRID 2079545ノート

反応式

HRID 2079545 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.[C:13]([O:17][CH3:18])(=[O:16])[CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.CCOCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:15]=[CH:14]/[C:13]([O:17][CH3:18])=[O:16])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1

参加物

8

反応物 3

HCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 27245244-Chloro-1-iodo-2-(trifluoromethyl)benzene

生成物 1

HCID 57657554(E)-Methyl 3-(4-chloro-2-(trifluoromethyl)phenyl)acrylate収率 100.4%

試薬・触媒・溶媒 4

HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

The mixture of 4-chloro-1-iodo-2-(trifluoromethyl)-benzene (15 g), methyl acrylate (6.74 g), tetrabutylammonium chloride (14 g), palladium acetate (0.22 g) and potassium carbonate (13.6 g) in DMF (150 ml) was stirred at room temperature for 4 days. After diluting with ether (1 L), the mixture was washed with water (5×200 ml), then dried over sodium sulphate and solvent removed under reduced pressure. The residue was columned on silica gel using 5:1 heptane:EtOAc as eluant to give (E)-methyl 3-(4-chloro-2-(trifluoromethyl)-phenyl)-acrylate (13 g).

後処理

  1. washthe mixture was washed with water (5×200 ml)
  2. dry with materialdried over sodium sulphate and solvent
  3. customremoved under reduced pressure

出典と根拠

ORDレコード
ord-b097aba6901c4812b28843bffa923585
出典データセット
uspto-grants-2011_04
特許番号
US07932251B2

反応ノート

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