Benzyl Bromide → Indole

HRID 2256240Notes

Reaction equation

HRID 2256240 reaction equation
C([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[C:9](OC)[CH:8]=[CH:7][CH:6]=2)C.[H-].[Na+].C(Br)C1C=CC=CC=1>CN(C=O)C.O>[NH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:3]1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 98556072-ethyl-4-methoxy-1H-indole

Product 1

HCID 798Indole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Ethyl-4-methoxy-1H-indole (4.2 g, 24 mmol) was dissolved in 30 mL of DMF and 960 mg (24 mmol) of 60% NaH/minerial oil was added. After 1.5 hours, 2.9 mL(24 mmol) of benzyl bromide was added. After 4 hours, the mixure was diluted with water and extracted twice with ethyl acetate. The combined ethyl acetate was washed with brine, dried (MgSO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 3.1 g (49% yield) of 2-ethyl-4-methoxy-1-phenylmethyl)-1H-indole.

Workup

  1. waitAfter 4 hours
  2. extractionextracted twice with ethyl acetate
  3. washThe combined ethyl acetate was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated at reduced pressure
  6. customThe residue was chromatographed on silica gel
  7. washeluted with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-cc85a86a8428445195fa71c073607366
Source dataset
uspto-grants-1997_08
Patent number
US05654326

Reaction notes

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