Water → 2'-Nitro[1,1'-biphenyl]-4-carbaldehyde

HRID 1865037Notes

Reaction equation

HRID 1865037 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH:11]([C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1)=[O:12].C(=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)C.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:16]1[CH:17]=[CH:18][C:13]([CH:11]=[O:12])=[CH:14][CH:15]=1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 113411-Bromo-2-nitrobenzeneHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 218367482'-Nitro[1,1'-biphenyl]-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178477754HCID 178477754, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Add 1-bromo-2-nitrobenzene (13.30 g, 65.83 mmol), 4-formylphenylboronic acid (10.89 g, 72.41 mmol), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.61 g, 1.97 mmol) and 2M aqueous sodium carbonate (164.57 mL, 329.15 mmol) in DMF, and heat to 80° C. with stirring. After 18 hours, cool and pour into water. Extract the mixture with ethyl acetate. Combine the organic extracts, and wash with water and brine, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Purify by flash chromatography eluting with methylene chloride to provide the title compound. 1H NMR (400 MHz; CDCl3) δ-10.02(s, 1H), 7.92-7.99(m, 3H), 7.65(t, 1H), 7.58(t, 1H), 7.44-7.49(m, 3H).

Workup

  1. temperaturecool
  2. extractionExtract the mixture with ethyl acetate
  3. washwash with water and brine
  4. dry with materialdry over anhydrous magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customPurify by flash chromatography
  8. washeluting with methylene chloride

Sources & evidence

ORD record
ord-a4511edf231c4bcb976fbf2c85cf8ddd
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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