Sodium Carbonate → 4-Methoxy-8-nitro-dibenzofuran-1-carbaldehyde

HRID 2427850Notes

Reaction equation

HRID 2427850 reaction equation
Br[C:2]1[C:9]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[C:8]([O:20][CH3:21])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:21][O:20][C:8]1[C:9]2[O:10][C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=3[C:2]=2[C:3]([CH:4]=[O:5])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 211057062-Bromo-4-methoxy-3-(4-nitrophenoxy)benzaldehyde

Product 1

HCID 211057134-Methoxy-8-nitro-dibenzofuran-1-carbaldehydeYield 58.9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

2-Bromo-4-methoxy-3-(4-nitro-phenoxy)-benzaldehyde (19.4 g, 55.1 mmoles) is dissolved in dry DMF (450 mL) under nitrogen atmosphere. Sodium carbonate (7.0 g, 66.11 mmoles) and palladium acetate (1.15 g, 5.1 mmoles) are added to the solution. The reaction mixture is heated at 130° C. for 18 hours. The crude is filtered and the mother liquor is poured in water. Precipitation occurs. The suspended solid is filtered, washed with water and dried under vacuum overnight to afford a pale brown solid (8.8 g).

Workup

  1. filtrationThe crude is filtered
  2. additionthe mother liquor is poured in water
  3. customPrecipitation
  4. filtrationThe suspended solid is filtered
  5. washwashed with water
  6. customdried under vacuum overnight

Sources & evidence

ORD record
ord-29ed1ffe66fa41a8b7161f71e47ba9e1
Source dataset
uspto-grants-2011_06
Patent number
US07968724B2

Reaction notes

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