tert-BUTYL CHLORIDE → 4-t-Butyl-1-(4-methylphenyl)pyrrole-2-carbonitrile

HRID 248377Notes

Reaction equation

HRID 248377 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2[C:13]#[N:14])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:19](Cl)([CH3:22])([CH3:21])[CH3:20]>ClCCl>[C:19]([C:11]1[CH:10]=[C:9]([C:13]#[N:14])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH:12]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 10486tert-BUTYL CHLORIDEHCID 27977151-(4-Methylphenyl)pyrrole-2-carbonitrileHCID 6451240Aluminum(III) Chloride

Product 1

HCID 197593174-t-Butyl-1-(4-methylphenyl)pyrrole-2-carbonitrileYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 1-(4-methylphenyl)pyrrole-2-carbonitrile (546 mg) and aluminum chloride (532 mg) in dichloromethane (10 ml) was added t-butyl chloride (368 mg) in dichloromethane (10 ml) in one portion at 5° C. The mixture was stirred at the same temperature for 20 minutes. The reaction mixture was quenched with 10% hydrochloric acid. The separated organic layer was washed with 10% hydrochloric acid and water, successively, dried, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluted by a mixture of ethyl acetate and n-hexane (1:6) to yield 4-t-butyl-1-(4-methylphenyl)pyrrole-2-carbonitrile (660 mg).

Workup

  1. customThe reaction mixture was quenched with 10% hydrochloric acid
  2. washThe separated organic layer was washed with 10% hydrochloric acid and water
  3. customsuccessively, dried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluted by a mixture of ethyl acetate and n-hexane (1:6)

Sources & evidence

ORD record
ord-47aab38b48c2450d9dc188b0d4da85ae
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

Loading…