Boron tribromide → 6-hydroxy-2,3-dihydro-1H-indol-2-one

HRID 1019156Notes

Reaction equation

HRID 1019156 reaction equation
C[O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 27937496-Methoxyoxindole

Product 1

HCID 27841396-hydroxy-2,3-dihydro-1H-indol-2-oneYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of 3.26 of 6-methoxy-2-oxindole in 60 mL of dischloromethane was cooled at −3° C. and 10 mL of 1 M boron tribromide solution in dichloromethane was added dropwise. The reaction mixture was stirred in ice-bath for 1 hour, room temperature for 1 hour, poured into ice water, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, concentrated, and dried in a vacuum oven overnight to give 2.56 g of the 6-hydroxy-2-oxindole (86% yield),

Workup

  1. waitroom temperature for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-dba2e507240e4efd9dea66ae4d4031cd
Source dataset
uspto-grants-2002_11
Patent number
US06486185B1

Reaction notes

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