Water → 4-Fluoro-5-(3-fluoro-benzoyl)-2-methoxy-benzonitrile

HRID 1610112ノート

反応式

HRID 1610112 の反応式
Br[C:2]1[C:3]([O:18][CH3:19])=[CH:4][C:5]([F:17])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[O:9])[CH:7]=1.O.[CH3:21][N:22](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:17][C:5]1[C:6]([C:8](=[O:9])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[CH:7][C:2]([C:21]#[N:22])=[C:3]([O:18][CH3:19])[CH:4]=1

参加物

7

反応物 3

HCID 962WaterHCID 6228DimethylformamideHCID 22260993(5-Bromo-2-fluoro-4-methoxy-phenyl)-(3-fluoro-phenyl)-methanone

生成物 1

HCID 222610354-Fluoro-5-(3-fluoro-benzoyl)-2-methoxy-benzonitrile

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
120 °C

実験手順

A total of 856 mg of (5-bromo-2-fluoro-4-methoxy-phenyl)-(3-fluoro-phenyl)-methanone obtained in Production Example II-1-b was dissolved in 13.1 ml of N,N-dimethylformamide, 185 mg of zinc cyanide, 13.6 mg of tris(dibenzylideneacetone)dipalladium and 17.4 mg of 1,1′-bis(diphenylphosphino)ferrocene were added thereto, and the mixture was stirred at 120° C. in an atmosphere of nitrogen gas for 7 hours. After cooling to room temperature, water was added to the reaction mixture and the mixture was extracted with diethyl ether. The resulting organic layer was washed with brine, dried over magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:2), to give 203 mg of the title compound as pale yellow crystals.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe resulting organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified
  7. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:2)

出典と根拠

ORDレコード
ord-4490057f1d6f45c387b0790156a129c8
出典データセット
uspto-grants-2006_01
特許番号
US06982274B2

反応ノート

読み込み中…