Hexachloroethane → HCID 59426450, compound

HRID 252574Notes

Reaction equation

HRID 252574 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[C:5]([C:16]#[N:17])=[CH:4]1)[CH3:2].[Li+].CC([N-]C(C)C)C.[Cl:26]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1>[Cl:26][C:4]1[N:3]([CH2:1][CH3:2])[C:11]2[C:6]([C:5]=1[C:16]#[N:17])=[CH:7][CH:8]=[C:9]([C:12]([F:13])([F:15])[F:14])[CH:10]=2

Participants

5

Reactant 3

HCID 6214HexachloroethaneHCID 2724682Lithium diisopropylamideHCID 59425545HCID 59425545, compound

Product 1

HCID 59426450HCID 59426450, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-ethyl-6-trifluoromethylindole-3-carbonitrile (2.54 g, 10.0 mmol), prepared by the method of procedure 1A, in anhydrous THF (20.0 mL), at −78° C. is added LDA (8.3 mL, 1.5 M mono-THF in cyclohexane, 12.5 mmol) dropwise. The mixture is continued for 0.5 h after the addition, followed by the addition of hexachloroethane and the mixture is then brought to room temperature slowly and stirred for 0.5 h. The solvent is then evaporated and the residue is treated with water. The organics are extracted with dichloromethane, washed with water and brine and dried over anhydrous Na2SO4. The crude product obtained after the removal of the solvent is chromatographed (silica gel, dichloromethane/hexanes, 3/2) to provide 2-chloro-1-ethyl-6-(trifluoromethyl)-1H-indole-3-carbonitrile (1.75 g, 64%).

Workup

  1. additionafter the addition
  2. customis then brought to room temperature
  3. customThe solvent is then evaporated
  4. additionthe residue is treated with water
  5. extractionThe organics are extracted with dichloromethane
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe crude product obtained
  9. customafter the removal of the solvent
  10. customis chromatographed (silica gel, dichloromethane/hexanes, 3/2)

Sources & evidence

ORD record
ord-72d84b7483ca42cc854e4d2bacaea62b
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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