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

HRID 269979

Reaction equation

HRID 269979 reaction equation
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

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-51ecd0902f6c43c5a2a4e4835813cd3a
Source dataset
uspto-grants-2008_11
Patent number
US07449477B2

Linked notes

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