Indole → 1-(2-chloroethyl)-1H-indole

HRID 1798015Notes

Reaction equation

HRID 1798015 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.Br[CH2:13][CH2:14][Cl:15].O>CCCCC.CN(C=O)C>[Cl:15][CH2:14][CH2:13][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

7

Reactant 4

HCID 798IndoleHCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydride2×

Product 1

HCID 108992601-(2-chloroethyl)-1H-indoleYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8003PentaneSolvent

Procedure

NaH (0.253 g; 0.11 mole of 60% NaH in suspension in mineral oil, previously washed with pentane) is added to a solution of indole (1.17 g; 0.1 mole) in 10 mL of DMF placed under a nitrogen atmosphere, then the reaction mixture is stirred for 30 minutes at ambient temperature. 1-bromo 2-chloroethane is then added. After reaction for 2 hours, the reaction mixture is treated by the slow addition of water and extracted with ethyl acetate. The organic phase is washed with water then with a saturated aqueous solution of NaCl, dried over anhydrous Na2SO4, filtered and evaporated under vacuum. The residue obtained is purified by chromatography on silica gel. The 1-(2-chloroethyl)indole is obtained pure with a yield of 80%.

Workup

  1. customAfter reaction for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialwith a saturated aqueous solution of NaCl, dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe residue obtained
  8. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a866812d3a264815a7c3a655b5b17cd0
Source dataset
uspto-grants-2013_01
Patent number
US08343964B2

Reaction notes

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