Cyclohexane → 3-(3-bromopropyl)-1H-indole

HRID 488763

Reaction equation

HRID 488763 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12]O)=[CH:2]1.[Br:14]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1CCCCC1>O1CCOCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][Br:14])=[CH:2]1

Participants

5

Reactant 3

HCID 8078CyclohexaneHCID 70579Triphenylphosphine dibromideHCID 77115Indole-3-propanol

Product 1

HCID 100371923-(3-bromopropyl)-1H-indoleYield 99.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2 g (11.41 mmol) of 3-(1H-indol-3-yl)propanol in 40 ml of dioxane was added at room temperature 5.3 g (12.55 mmol) of dibromotriphenylphosphorane and the resulting solution was stirred during 18 h. An excess of cyclohexane was added and the resulting precipitate was filtered and discarded. The solvent was evaporated to dryness to give 2.7 g (99%) of product as an oil which was used in the subsequent step without further purification.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-95a92f9deef44427874f44288a58b4e1
Source dataset
uspto-grants-2005_12
Patent number
US06974819B2

Linked notes

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