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

HRID 503156노트

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HRID 503156 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

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

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온도
120 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-17c956c663db43bc8530f0c5a52c71f6
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776890B2

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