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

HRID 1713859ノート

反応式

HRID 1713859 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl触媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a552d6c04b8848d1983e7b9454fe2453
出典データセット
uspto-grants-2010_09
特許番号
US07795283B2

反応ノート

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