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

HRID 269979

반응식

HRID 269979 반응식
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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-51ecd0902f6c43c5a2a4e4835813cd3a
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449477B2

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