Water → 4-Methoxy-8-nitro-dibenzofuran-1-carbaldehyde

HRID 131585Notes

Reaction equation

HRID 131585 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+].O>CC(N(C)C)=O.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

6

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 211057062-Bromo-4-methoxy-3-(4-nitrophenoxy)benzaldehyde

Product 1

HCID 211057134-Methoxy-8-nitro-dibenzofuran-1-carbaldehydeYield 144.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
170 °C

Procedure

2-Bromo-3-(p-nitrophenoxy)-4-methoxy benzaldehyde (3.5 gm, 0.0087 mol), anhydrous sodium carbonate (1.125 gm, 0.0106 mol) and palladium (II) acetate (0.19 gm, 0.0008 mol), in dimethylacetamide (15 ml) are heated and stirred under nitrogen at 170° C. for 2 h. Water (90 ml) is added to the cooled reaction mixture. The precipitated solid is collected by filteration and washed with 5% hydrochloric acid followed by water. The product was obtained as a yellow solid (3.4 gm).

Workup

  1. customThe precipitated solid is collected by filteration
  2. washwashed with 5% hydrochloric acid

Sources & evidence

ORD record
ord-9c3139cf5033442d8f6ca6581190d0ea
Source dataset
uspto-grants-2008_06
Patent number
US07384962B2

Reaction notes

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