Methyl iodide → 1-Acetyl-6-bromo-3,3-dimethylindolin-2-one

HRID 1942534Notes

Reaction equation

HRID 1942534 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:13])[CH:11]=2)[CH:6]([CH3:14])[C:5]1=[O:15])(=[O:3])[CH3:2].[H-].[Na+].CI.[CH2:20]1COCC1>O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:13])[CH:11]=2)[C:6]([CH3:20])([CH3:14])[C:5]1=[O:15])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 108257591-acetyl-6-bromo-3-methyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 108267191-Acetyl-6-bromo-3,3-dimethylindolin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1-acetyl-6-bromo-3-methyl-1,3-dihydro-2H-indol-2-one (9.5 g) were added NaH (1.57 g), methyl iodide (2.45 ml) and THF (70 ml) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. After the reaction was complete, water was added to the reaction solution, and the mixture was extracted with ethyl acetate solution. 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 (5.2 g) as a colorless crystal.

Workup

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

Sources & evidence

ORD record
ord-6aae1b14ef714dce8814ba9c97231da7
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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