Boron tribromide → 2-(4-Hydroxyphenyl)-1H-indol-5-ol

HRID 1375331Notes

Reaction equation

HRID 1375331 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]1[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=1)=[CH:6]2.B(Br)(Br)Br>C(Cl)Cl.C([O-])(O)=O.[Na+]>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[CH:6]2

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 12398997HCID 12398997, compound

Product 1

HCID 134083752-(4-Hydroxyphenyl)-1H-indol-5-olYield 79.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

Five g (18.7 mmol) of 5-methoxy 2-(4 methoxyphenyl)indole was dissolved in 30 mL CH2Cl2 under argon, cooled on dry ice/acetone and 70 mL 1 M BBr3 were added with stirring. The solution was warmed to 0° C. for 30 min. It was then stirred at room temperature overnight. The reaction mixture was suspended in sat. NaHCO3 solution and extracted with CH2Cl2 (2×). The organic extract was washed with brine and dried over Na2SO4. Removal of the solvent in vacuo and flash chromatography (5% MeOH in CH2Cl2) gave 3.33 g of 3.

Workup

  1. additionwere added
  2. stirringIt was then stirred at room temperature overnight
  3. extractionextracted with CH2Cl2 (2×)
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over Na2SO4
  7. customRemoval of the solvent in vacuo and flash chromatography (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-f0b49813d5484534a8f6b92f8d3ac096
Source dataset
uspto-grants-2007_01
Patent number
US07169611B2

Reaction notes

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