Sodium Sulfite → 1H-Indol-3-ol, 1-acetyl-5-bromo-

HRID 239010Notes

Reaction equation

HRID 239010 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:13])=[CH:10][CH:11]=2)[C:6]([O:14]C(=O)C)=[CH:5]1)(=[O:3])[CH3:2].S([O-])([O-])=O.[Na+].[Na+]>O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:13])=[CH:10][CH:11]=2)[C:6]([OH:14])=[CH:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24437Sodium SulfiteHCID 118505N-Acetyl-5-bromoindolyl acetate

Product 1

HCID 27352351H-Indol-3-ol, 1-acetyl-5-bromo-Yield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

1-acetyl-5-bromo-3-acetoxyindole (1.0 g, 3.38 mmol) and sodium sulfite (1.0 g, 7.94 mmol) were mixed in 20 ml water. After heated for 3 hours at 80° C., the reaction mixture was cooled down to room temperature, and then extracted with ethyl acetate (50 ml×2). The combined organic phases were dried and evaporated to obtain a solid as white needles (1-acetyl-5-bromo-3-hydroxyindole) (0.7 g, yield: 82%; mp: 180-182° C.).

Workup

  1. temperaturethe reaction mixture was cooled down to room temperature
  2. extractionextracted with ethyl acetate (50 ml×2)
  3. customThe combined organic phases were dried
  4. customevaporated

Sources & evidence

ORD record
ord-66d5718b03344212b457772f11c45443
Source dataset
uspto-grants-2014_02
Patent number
US08642765B2

Reaction notes

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