2-Bromopropane → 4-Isopropyloxy dibenzo[b,d]furan-1-carbaldehyde

HRID 1293436Notes

Reaction equation

HRID 1293436 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+].[CH:23](Br)([CH3:25])[CH3:24]>CN(C=O)C.O>[CH: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)([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 442251964-Hydroxy dibenzo[b,d]furan-1-carbaldehyde

Product 1

HCID 859670564-Isopropyloxy dibenzo[b,d]furan-1-carbaldehydeYield 100.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

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 isopropyl bromide (431 mg, 3.537mmol) and the reaction mixture was stirred for 4 hrs. 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 (600 mg).

Workup

  1. stirringthe reaction mixture was stirred for 4 hrs
  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-45606bb9fb334ca990abdf0dc21c9ef1
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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