Indole → 1-(3-Bromopropyl)indole

HRID 345672Notes

Reaction equation

HRID 345672 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].[Br:12][CH2:13][CH2:14][CH2:15]Br>CN(C=O)C>[Br:12][CH2:13][CH2:14][CH2:15][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 798IndoleHCID 80011,3-DibromopropaneHCID 14797Potassium Hydroxide

Product 1

HCID 118590271-(3-Bromopropyl)indoleYield 30.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 23.4 g of indole in 200 ml of DMF, cooled to 10° C., were added 22.4 g of potassium hydroxide and 101 g of 1,3-dibromopropane. The mixture was stirred under nitrogen for 3 days. The solid formed was filtered off and the filtrate was evaporated. The residue was chromatographed on silica gel with 5% diethyl ether in petroleum ether to give 14.7 g of 1-(3-bromopropyl)indole.

Workup

  1. customThe solid formed
  2. filtrationwas filtered off
  3. customthe filtrate was evaporated
  4. customThe residue was chromatographed on silica gel with 5% diethyl ether in petroleum ether

Sources & evidence

ORD record
ord-f8b4a65cde2d44a4a8c9c3f7021859b5
Source dataset
uspto-grants-1991_10
Patent number
US05057614

Reaction notes

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