Diethyl Malonate → Diethyl (4'-nitrobiphenyl-4-yl)malonate

HRID 1713859노트

반응식

HRID 1713859 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:23]([O:31][CH2:32][CH3:33])(=[O:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:23]([O:31][CH2:32][CH3:33])=[O:30])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)([O-:16])=[O:15]

참가 물질

7

반응물 3

HCID 7761Diethyl MalonateHCID 10796Cesium carbonateHCID 2336104-Bromo-4'-nitro-1,1'-biphenyl

생성물 1

HCID 59464037Diethyl (4'-nitrobiphenyl-4-yl)malonate수율 101.7%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl촉매HCID 1140Toluene용매

실험 절차

A mixture of 4-(4-bromophenyl)nitrobenzene (Journal of Organic Chemistry, 2005, 70(9), 3730) (800 mg, 2.88 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (Xphos) (69 mg) and caesium carbonate (2.81 g, 8.63 mmol) in toluene (40 mL) was deoxygenated then palladium(II) acetate (13 mg, 0.06 mmol) and diethyl malonate (0.480 mL, 3.2 mmol) were added. The reaction mixture was heated under reflux for 2 h, cooled and then filtered through diatomaceous earth and the filter washed with EtOAc. The filtrate was concentrated by evaporation and adsorbed onto silica then purified by chromatography, eluting with 0-25% EtOAc in isohexane, to give the title compound (1.047 g) as a solid.

후처리

  1. customwas deoxygenated
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 2 h
  4. temperaturecooled
  5. filtrationfiltered through diatomaceous earth
  6. washthe filter washed with EtOAc
  7. concentrationThe filtrate was concentrated by evaporation
  8. customthen purified by chromatography
  9. washeluting with 0-25% EtOAc in isohexane

출처 및 근거

ORD 기록
ord-a552d6c04b8848d1983e7b9454fe2453
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795283B2

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