Toluene → 3-(5-Chloro-3'-nitro-biphenyl-2-yl)-propionaldehyde

HRID 269979

反応式

HRID 269979 の反応式
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1N.[N+:10]([C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1)([O-:12])=[O:11].[C:22]([O-:25])([O-])=O.[Na+].[Na+].[C:28]1(C)C=CC=C[CH:29]=1>CCO.O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:8][C:6]1[CH:7]=[CH:2][C:3]([CH2:28][CH2:29][CH:22]=[O:25])=[C:4]([C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=2)[CH:5]=1

参加物

9

反応物 4

HCID 1140TolueneHCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 701102-Bromo-4-chloroaniline

生成物 1

HCID 860554083-(5-Chloro-3'-nitro-biphenyl-2-yl)-propionaldehyde

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Heat a mixture of 2-bromo-4-chloro-phenylamine (8.24 g, 40 mmol), 3-nitrophenylboronic acid (10.0 g, 60 mmol), Pd(PPh3)4 (2.8 g) and Na2CO3 (17.0 g) in toluene (200.0 mL), EtOH (30.0 mL) and water (80.0 mL) to 80° C. (oil bath) with stirring overnight. Cool to room temperature, dilute the mixture with EtOAc, filter and concentrate. Dissolve the residue in EtOAc, wash with brine and dry over Na2SO4. Chromatograph the crude material on silica (gradient 25% EtOAc in hexane) to give 5.27 g of the desired product as a yellowish crystal.

後処理

  1. temperatureHeat
  2. filtrationfilter
  3. concentrationconcentrate
  4. dissolutionDissolve the residue in EtOAc
  5. washwash with brine
  6. dry with materialdry over Na2SO4

出典と根拠

ORDレコード
ord-51ecd0902f6c43c5a2a4e4835813cd3a
出典データセット
uspto-grants-2008_11
特許番号
US07449477B2

関連ノート

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