Indole → 1-(2-chloroethyl)-1H-indole

HRID 1108539Notes

Reaction equation

HRID 1108539 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.C1(C)C=CC(S(O[CH2:22][CH2:23][Cl:24])(=O)=O)=CC=1>O1CCCC1>[Cl:24][CH2:23][CH2:22][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

5

Reactant 3

HCID 798IndoleHCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 24758Sodium hydride

Product 1

HCID 108992601-(2-chloroethyl)-1H-indoleYield 40.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

An oil dispersion (7.2 g) of sodium hydride (0.21 mol) and tetrahydrofuran (50 ml) were placed in a 500-ml flask equipped with a stirrer and a condenser tube, and the mixture was stirred in an ice-water bath. Indole (24.60 g, 0.21 mol) dissolved in tetrahydrofuran (100 ml) was gradually added dropwise to the mixture. After completion of addition, the ice-water bath was removed, and the mixture was stirred for one hour at room temperature. Subsequently, 2-chloroethyl p-toluenesulfonate (49.29 g, 0.21 mol) was added, and the mixture was allowed to react for 15 hours while being stirred under heat-reflux conditions. After completion of reaction, insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The reaction mixture was purified by silica gel column chromatography to obtain 1-(2-chloroethyl)indole (15.4 g).

Workup

  1. customequipped with a stirrer and a condenser tube
  2. additionwas gradually added dropwise to the mixture
  3. additionAfter completion of addition
  4. customthe ice-water bath was removed
  5. stirringthe mixture was stirred for one hour at room temperature
  6. customto react for 15 hours
  7. stirringwhile being stirred under heat-reflux conditions
  8. customAfter completion of reaction, insoluble matter
  9. customwas removed by filtration
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe reaction mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f00fe870ffa946e1982f167fe02e7f4a
Source dataset
uspto-grants-2000_05
Patent number
US06068963

Reaction notes

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