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Ethyl bromoacetate → 4-Ethoxycarbomethoxy dibenzo[b,d]furan-1-carbaldehyde

HRID 1293442
Notes
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Reaction equation

HRID 1293442 reaction equation
O[C:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[C:5]([CH:15]=[O:16])=[CH:4][CH:3]=1.[C:17](=O)([O-])[O-:18].[K+].[K+].[CH2:23]([O:25][C:26](=[O:29])CBr)[CH3:24]>CN(C=O)C.O>[CH2:23]([O:25][CH2:26][O:29][C:17]([C:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[C:5]([CH:15]=[O:16])=[CH:4][CH:3]=1)=[O:18])[CH3:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 442251964-Hydroxy dibenzo[b,d]furan-1-carbaldehyde

Product 1

HCID 859669124-Ethoxycarbomethoxy dibenzo[b,d]furan-1-carbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
80 °C

Procedure

Intermediate 19 (500 mg, 2.358 mmol) was dissolved in dry DMF (5 ml). Anhydrous potassium carbonate (650 mg, 4.716 mmol) was added to the above solution and was stirred for 10 min. at 80° C. To this was added ethylbromoacetate (2.0 eq.) and the reaction mixture was stirred for 1 h. The reaction mixture was cooled to room temperature and diluted with water (100 ml) and extracted with ethyl acetate (3×50 ml). The organic extract was washed with water (50 ml) and brine solution (25 ml) and dried over anhydrous sodium sulfate. Removal of solvent gave the product as a white solid (550 mg).

Workup

  1. stirringthe reaction mixture was stirred for 1 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. extractionThe organic extract
  5. washwas washed with water (50 ml) and brine solution (25 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-7b6bda4b8c9a4e1db90a5b6dde933d79
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07238725B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes