Indole → 1-(2-chloroethyl)-1H-indole

HRID 2228368Notes

Reaction equation

HRID 2228368 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.[Cl:12][CH2:13][CH2:14]OS(C1C=CC(C)=CC=1)(=O)=O>O1CCCC1>[Cl:12][CH2:13][CH2:14][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

Into a flask of 500 ml capacity fitted with a stirrer and cooling tube, there were introduced 7.2 g (corresponding to 0.21 mol) of an oil dispersion of NaH and 50 ml of tetrahydrofuran, and the mixture was stirred on an ice-water bath. Into this mixture there was added dropwise, little by little, a solution in which 24.60 g (0.21 mol) of indole were dissolved in 100 ml of tetrahydrofuran. After completion of the dropwise addition, the ice-water bath was removed and the mixture was stirred for one hour at room temperature. Then, 49.29 g (0.21 mol) of 2-chloroethyl-p-toluene sulfonate were added, and the reaction performed under heated reflux whilst stirring for 15 hours. After completion of the reaction, the undissolved material was removed by filtration, and concentration was performed under reduced pressure. This reaction mixture was purified by column chromatography using silica gel, to obtain 15.4 g of 1-(2-chloroethyl)indole.

Workup

  1. customInto a flask of 500 ml capacity fitted with a stirrer
  2. temperaturecooling tube
  3. additionInto this mixture there was added dropwise
  4. additionAfter completion of the dropwise addition
  5. customthe ice-water bath was removed
  6. stirringthe mixture was stirred for one hour at room temperature
  7. temperatureunder heated
  8. temperaturereflux
  9. stirringwhilst stirring for 15 hours
  10. customAfter completion of the reaction
  11. customthe undissolved material was removed by filtration, and concentration
  12. customThis reaction mixture was purified by column chromatography

Sources & evidence

ORD record
ord-4d92950e24ef448e9dca9402ceaf3ef3
Source dataset
uspto-grants-2002_07
Patent number
US06416939B1

Reaction notes

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