Ethyl Bromide → 5-Chloro-1-ethyl-1H-indole

HRID 352769Notes

Reaction equation

HRID 352769 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[OH-].[Na+].Br[CH2:14][CH3:15].[Cl-].[NH4+]>C1C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:14][CH3:15])[CH:6]=[CH:5]2

Participants

9

Reactant 4

HCID 6332Ethyl BromideHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 871105-Chloroindole

Product 1

HCID 178991595-Chloro-1-ethyl-1H-indole

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 241BenzeneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In benzene (10 ml), 5-chloroindole (1.52 g) was dissolved, followed by the addition of a 50% aqueous solution of sodium hydroxide (10 ml), tetrabutylammonium bromide (161 mg) and bromoethane (1.64 g). The resulting mixture was stirred at room temperature for 40 hours. After the addition of a saturated aqueous solution of ammonium chloride to the reaction mixture, water and dichloromethane were added to separate the organic layer. After the organic layer was dried over anhydrous sodium sulfate, the residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (ethyl acetate:hexane 1:20), whereby the title compound (1.68 g, 93%) was obtained as colorless crystals.

Workup

  1. additionwere added
  2. customto separate the organic layer
  3. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  4. customthe residue obtained
  5. distillationby distilling off the solvent under reduced pressure
  6. customwas purified by chromatography on a silica gel column (ethyl acetate:hexane 1:20), whereby the title compound (1.68 g, 93%)
  7. customwas obtained as colorless crystals

Sources & evidence

ORD record
ord-2e911a448d0a4262bb4894d8483d07f1
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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