Benzyl Bromide → 4-Benzyloxy dibenzo[b,d]furan-1-carbaldehyde

HRID 1293437Notes

Reaction equation

HRID 1293437 reaction equation
[OH:1][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(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C.O>[CH2:23]([O:1][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:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 442251964-Hydroxy dibenzo[b,d]furan-1-carbaldehyde

Product 1

HCID 859670584-Benzyloxy dibenzo[b,d]furan-1-carbaldehydeYield 90.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Intermediate 19 (1 gm, 5.10 mmol) was dissolved in dry DMF (10 ml). Anhydrous potassium carbonate (1.05 gm, 7.65 mmol) was added to the above solution and was stirred for 10 min. at 80° C. To this was added benzyl bromide (0.87 gm, 5.10 mmol) and the reaction mixture was stirred for 2 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 brown solid (1.4 gm).

Workup

  1. stirringthe reaction mixture was stirred for 2 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-3d637748b5774261b7e6761ed5ec0bd7
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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