Boron tribromide → 6-Hydroxyindole

HRID 1836658Notes

Reaction equation

HRID 1836658 reaction equation
C[O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 766596-Methoxy-1H-indole

Product 1

HCID 5245086-Hydroxyindole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Methoxyindole (1.47 g, 10.00 mmol) was cooled to 0° C. in methylene chloride and BBr3 (2 M in methylene chloride, 25 mL, 50.00 mmol) was added. After stirring 16 h at room temperature, TLC analysis indicated the reaction was complete. The reaction was quenched with water and the layers separated. The organic layers were washed with 1 N NaOH. The basic aqueous layers were acidified with conc. HCL, extracted with methylene chloride, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the crude 6-hydroxyindole which was used directly for the next reaction.

Workup

  1. customThe reaction was quenched with water
  2. customthe layers separated
  3. washThe organic layers were washed with 1 N NaOH
  4. extractionextracted with methylene chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99b017107f31491986d9e36245860446
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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