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

HRID 1952949Notes

Reaction equation

HRID 1952949 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 coold 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. customwas coold at -3° C.
  2. waitroom temperature for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-d59fd17e9b6749c19feb6322a582caa7
Source dataset
uspto-grants-2000_09
Patent number
US06114371

Reaction notes

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