Hexachloroethane → HCID 59426450, compound

HRID 907182Notes

Reaction equation

HRID 907182 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. was added LDA (8.3 mL, 1.5 M mono-THF in cyclohexane, 12.5 mmol) dropwise. The mixture was continued for 0.5 hr after the addition, followed by the addition of hexachloroethane and the mixture was then brought to room temperature slowly and stirred for 0.5 hr. The solvent was then evaporated and the residue was treated with water. The organics were extracted with dichloromethane, washed with water and brine and dried over anhydrous Na2SO4. The crude product obtained after the removal of the solvent was 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. customwas then brought to room temperature
  3. customThe solvent was then evaporated
  4. additionthe residue was treated with water
  5. extractionThe organics were 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. customwas chromatographed (silica gel, dichloromethane/hexanes, 3 /2)

Sources & evidence

ORD record
ord-921bdddf6c424777a9dc44f37e4694a3
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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