Potassium Iodide → 6-Bromo-1-(4-methoxybutyl)-3,3-dimethyl-1,3-dihydro-2H-indol-2-one

HRID 1942536Notes

Reaction equation

HRID 1942536 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:13])([CH3:12])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.CN([CH:17]=[O:18])C.[H-].[Na+].[I-].[K+]>O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:13])([CH3:12])[C:7](=[O:11])[N:8]2[CH2:10][CH2:2][CH2:3][CH2:4][O:18][CH3:17])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 106576496-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-2-one

Product 1

HCID 583762346-Bromo-1-(4-methoxybutyl)-3,3-dimethyl-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 6-bromo-3,3-dimethyl-1,3-dihydro-2H-indol-2-one (1.5 g) were added DMF (24 mL) and NaH (326 mg) under ice-cooling, and the mixture was stirred at room temperature 15 minutes. Then, to the mixture were added 4-chloromethyl butyl ether (1.54 g) and potassium iodide (208 mg), and the mixture was stirred at 100° C. for 7 hours. After the reaction was complete, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. This ethyl acetate solution was washed with water and an aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give the title compound (1.87 g) as a colorless liquid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 100° C. for 7 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThis ethyl acetate solution was washed with water
  5. dry with materialan aqueous sodium chloride solution, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-10c700d350e14e6bbda95cd6a195b825
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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