1,5-Dibromopentane → HCID 67301893, compound

HRID 1015428Notes

Reaction equation

HRID 1015428 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 754211H-indol-4-ol

Product 1

HCID 67301893HCID 67301893, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred suspension of 4-hydroxyindole (10.0 g, 75.2 mmol) and 1,5-dibromo-pentane (26.0 g, 112.8 mmol) in N-methylpyrrolidinone (100 mL) was added potassium carbonate (16.0 g, 112.8 mmol). The resulting mixture was stirred at 90° C. for 4 hours and then quenched with water (30 mL) followed by extraction with ethyl acetate (30 mL×3). The organic layers were combined, washed with brine, and then concentrated under vacuum. The resulting residue was purified by silica gel chromotography to give 4-(5-bromo-pentyloxy)-1H-indole (14.0 g, 49.6 mmol, 66%) as a white solid.

Workup

  1. customquenched with water (30 mL)
  2. extractionfollowed by extraction with ethyl acetate (30 mL×3)
  3. washwashed with brine
  4. concentrationconcentrated under vacuum
  5. customThe resulting residue was purified by silica gel chromotography

Sources & evidence

ORD record
ord-810a39fd92c248ea810ccf8245a45add
Source dataset
uspto-grants-2011_07
Patent number
US07985763B2

Reaction notes

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