Dichloromethane → 4'-Formyl-2'-nitrobiphenyl-2-carbonitrile

HRID 519876

반응식

HRID 519876 반응식
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1OB(O)O)#[N:14].ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(C)C=CC=CC=1>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([C:16]2[C:15]([C:13]#[N:14])=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1)=[O:7]

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 8087924-Bromo-3-nitrobenzaldehydeHCID 217080892-Cyano-phenylboric acid

생성물 1

HCID 866440744'-Formyl-2'-nitrobiphenyl-2-carbonitrile수율 47%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 1140Toluene용매

실험 절차

A mixture of 4-bromo-3-nitrobenzaldehyde (10.0 g), 2-cyanophenylboric acid (8.25 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), dichloromethane adduct (3.45 g), tetrabutylammonium bromide (1.36 g), 2M aqueous sodium carbonate solution (40 mL) and toluene (400 mL) was refluxed under an argon atmosphere for 3 days. The reaction mixture was concentrated, and the residue was dissolved in ethyl acetate. The obtained ethyl acetate solution was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a pale-yellow solid (5.15 g, 40%).

후처리

  1. temperaturewas refluxed under an argon atmosphere for 3 days
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe obtained ethyl acetate solution was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-19142a26a34e481abc610366d05741bc
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115136B2

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