Sodium Cyanide → 3,4-Difluorobenzoylacetonitrile

HRID 46556

반응식

HRID 46556 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5](=[O:8])[CH2:6]Br.[C-]#N.[Na+].ClC1C=C(Cl)C=CC=1C(C[C:22]#[N:23])=O.C(C1C=CC=CC=1C(CC#N)=O)C.C(C1C=CC(C(CC#N)=O)=CC=1)(C)C.C(C1C=C(C=CC=1)C(CC#N)=O)C(C)C.CC1C=C(C=CC=1C)C(CC#N)=O.C(OC1C=C(C=CC=1)C(CC#N)=O)C.C(OC1C=CC(C(CC#N)=O)=CC=1)(C)C.C(OC1C=C(C=CC=1OCC)C(CC#N)=O)C.FC1C=CC(F)=CC=1C(CC#N)=O>O.C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5]([CH2:6][C:22]#[N:23])=[O:8]

참가 물질

14

반응물 11

HCID 8929Sodium CyanideHCID 27370322-Bromo-1-(3,4-difluorophenyl)ethan-1-oneHCID 43528863-Oxo-3-(4-(propan-2-yl)phenyl)propanenitrileHCID 125401753-(2,5-Difluorophenyl)-3-oxopropanenitrileHCID 136307283-(2,4-Dichlorophenyl)-3-oxopropanenitrileHCID 20387494m-IsobutylbenzoylacetonitrileHCID 203875023-(3,4-Dimethylphenyl)-3-oxopropanenitrileHCID 203875043-(3-Ethoxyphenyl)-3-oxopropanenitrileHCID 203875073,4-DiethoxybenzoylacetonitrileHCID 203875093-(2-Ethyl-phenyl)-3-oxo-propionitrileHCID 203875144-(1-Methylethoxy)-beta-oxobenzenepropanenitrile

생성물 1

HCID 27582543,4-Difluorobenzoylacetonitrile

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

A solution of 13.2 g. (0.056 mole) of 3,4-difluorophenacyl bromide was dissolved in 100 ml. of ethanol and cooled to 5° C. in ice. A solution of 7.6 g. (0.16 mole) of sodium cyanide in 40 ml. of water was added dropwise over 0.5 hr. and the reaction is stirred for an additional one hour. At that time, the mixture was diluted with 100 ml. of water and filtered through Celite®. Acidification of the filtrate gave a cloudy mixture which was extracted with methylene chloride. The organic phase was dried, filtered through Magnesol® and evaporated. Recrystallization of the residue from carbon tetrachloride provides 5.3 g. (52%) of colorless solid, m.p. 74°-75° C. Similarly prepared were 2,4-dichlorobenzoylacetonitrile, o-ethylbenzoylacetonitrile, p-isopropylbenzoylacetonitrile, m-isobutylbenzoylacetonitrile, 3,4-dimethylbenzoylacetonitrile, m-ethoxybenzoylacetonitrile, p-isopropoxybenzoylacetonitrile, 3,4-diethoxybenzoylacetonitrile, and 2,5-difluorobenzoylacetonitrile.

후처리

  1. additionAt that time, the mixture was diluted with 100 ml
  2. filtrationof water and filtered through Celite®
  3. customAcidification of the filtrate gave a cloudy mixture which
  4. extractionwas extracted with methylene chloride
  5. customThe organic phase was dried
  6. filtrationfiltered through Magnesol®
  7. customevaporated
  8. customRecrystallization of the residue from carbon tetrachloride
  9. customprovides 5.3 g
  10. customSimilarly prepared

출처 및 근거

ORD 기록
ord-46c5ea2bab6c41c3b7fdd1b63e77ae47
출처 데이터셋
uspto-grants-1979_11
특허 번호
US04173650

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