Water → 2-Nitrobiphenyl-4-carbaldehyde

HRID 1713322Notes

Reaction equation

HRID 1713322 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O>[N+:10]([C:3]1[CH:4]=[C:5]([CH:6]=[O:7])[CH:8]=[CH:9][C:2]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 8087924-Bromo-3-nitrobenzaldehyde

Product 1

HCID 118170112-Nitrobiphenyl-4-carbaldehydeYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

4-Bromo-3-nitrobenzaldehyde (2.0 g) was suspended in N,N-dimethylformamide (30 mL), phenylboronic acid (1.3 g), sodium carbonate (1.8 g), water (6 mL) and tetrakis-(triphenylphosphine)palladium(0) (1.0 g) were added, and the resulting mixture was stirred at 90° C. for 17 hours. The reaction mixture was cooled to room temperature and then partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was washed successively with water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1) to give the title compound (1.6 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate (100 mL) and water (100 mL)
  3. washThe organic layer was washed successively with water (50 mL) and brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-79b835c7ba184bac965e18352ee6a705
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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