Methanol → 5-Bromo-4-methoxy-1-methyl-1,3-dihydro-indol-2-one

HRID 1623537Notes

Reaction equation

HRID 1623537 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][C:6](=[O:13])[N:7]2[CH3:12].CO.[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.ClCCl.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>[Br:16][C:11]1[C:3]([O:2][CH3:1])=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:12])[C:6](=[O:13])[CH2:5]2

Participants

8

Reactant 3

HCID 887MethanolHCID 67184N-bromobutanimideHCID 127130311,3-Dihydro-4-methoxy-1-methyl-2H-indol-2-one

Product 1

HCID 667888735-Bromo-4-methoxy-1-methyl-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 4

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 24477Sodium ThiosulfateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 4-methoxy-1-methyl-1,3-dihydro-indol-2-one (440 mg, 2.483 mmol) in chloroform (25 ml) was added methanol (25.00 ml). The reaction was put at −10° C. and N-bromosuccinimide (442 mg, 2.483 mmol) was added in three portions over a 30 min interval and the reaction was then stirred for 10 minutes. The reaction was then diluted with dichloromethane, saturated aqueous sodium bicarbonate, and saturated aqueous sodium thiosulfate and the layers were separated. The aqueous layer was extracted two additional times with dichloromethane and the organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 60%) to afford 5-bromo-4-methoxy-1-methyl-1,3-dihydro-indol-2-one; MS: (ES+) m/z 255.8 (M+H)+.

Workup

  1. customwas put at −10° C.
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted two additional times with dichloromethane
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 60%)

Sources & evidence

ORD record
ord-76b0c80231814440b8c7fae942ac80e6
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

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