Benzyl Bromide → 4-(phenylmethoxy)-1H-indole

HRID 430773

Reaction equation

HRID 430773 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH2:13]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl Bromide2×HCID 14797Potassium HydroxideHCID 754211H-indol-4-ol

Product 1

HCID 884654-(phenylmethoxy)-1H-indoleYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium hydroxide (0.42 g) was added to 4-hydroxyindole (1.00 g) in DMF (25 ml), and the solution was stirred at room temperature for 15 minutes. Benzyl bromide (1.00 ml) was added to the solution, and the solution was stirred at room temperature for 1.5 hours. Since the reaction was not completed, benzyl bromide (0.20 ml) was further added and the solution was stirred for 5 hours. After removing the solvent under reduced pressure, water (50 ml) was added to the residue and the resultant was extracted with ether (3×50 ml). The organic layers were washed with saturated brine, and dried over sodium sulfate. After removing solids by filtration, the solvent was removed under reduced pressure and the obtained crude product was purified by silica gel column chromatography to obtain the desired product (1.43 g, yield: 85%).

Workup

  1. stirringthe solution was stirred at room temperature for 1.5 hours
  2. stirringthe solution was stirred for 5 hours
  3. customAfter removing the solvent under reduced pressure, water (50 ml)
  4. additionwas added to the residue
  5. extractionthe resultant was extracted with ether (3×50 ml)
  6. washThe organic layers were washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. customAfter removing solids
  9. filtrationby filtration
  10. customthe solvent was removed under reduced pressure
  11. customthe obtained crude product
  12. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ded0112ca83f4afa952d72e5c70ce665
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Linked notes

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