Benzyl Bromide → 1H-Indol-5-ol, 1-(phenylmethyl)-

HRID 2256263Notes

Reaction equation

HRID 2256263 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:7]=[CH:6]2

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 138725-MethoxyindoleHCID 24758Sodium hydrideHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 107754621H-Indol-5-ol, 1-(phenylmethyl)-Yield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

5-Methoxy-1H-indole (5.6 g, 21.5 mmol) was reacted with 1.0 g (25 mmol) of 60% sodium hydride and then 3.0 mL (25 mmol) of benzyl bromide by the method described in Example 12, Part D to give crude 5-methoxy-1-(phenylmethyl)-1H-indole. This material was dissolved in 250 mL of methylene chloride, cooled to -5° C., 50 mL of 1M BBr3 /CH2Cl2 added, the cooling bath removed and the mixture stirred for 1.75 hours. Ice water was added and the mixture stirred. The organic layer was separated, washed wish saturated NaCl, dried (Na2SO4), and concentrated at reduced pressure. The residue was chromatographed on silica gel and eluted with 20% ether/hexane→ether to give 870 mg (19% overall yield) of crude 5-hydroxy-1-(phenylmethyl)-1H-indole.

Workup

  1. customto give crude 5-methoxy-1-(phenylmethyl)-1H-indole
  2. customthe cooling bath removed
  3. additionIce water was added
  4. stirringthe mixture stirred
  5. customThe organic layer was separated
  6. washwashed
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated at reduced pressure
  9. customThe residue was chromatographed on silica gel
  10. washeluted with 20% ether/hexane

Sources & evidence

ORD record
ord-1be2f3a77f4045749fb149efa1e9b150
Source dataset
uspto-grants-1997_08
Patent number
US05654326

Reaction notes

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