tert-BUTYL CHLORIDE → HCID 12415108, compound

HRID 2306095Notes

Reaction equation

HRID 2306095 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]#[N:7].[C:8](Cl)([CH3:11])([CH3:10])[CH3:9].[Al]>[Cl-].[Ga+3].[Cl-].[Cl-]>[C:8]([C:4]1[CH:3]=[C:2]([C:6]#[N:7])[NH:1][CH:5]=1)([CH3:11])([CH3:10])[CH3:9].[C:8]([C:5]1[NH:1][C:2]([C:6]#[N:7])=[CH:3][CH:4]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 10486tert-BUTYL CHLORIDEHCID 138277Pyrrole-2-carbonitrileHCID 5359268Aluminum

Product 2

HCID 12415108HCID 12415108, compoundHCID 18434424HCID 18434424, compound

Reagents, catalysts & solvents 1

HCID 186022Gallium monochlorideCatalyst

Procedure

Friedel-Crafts alkylation reactions have been utilized by prior workers to synthesize 4-substituted-pyrrole-2-carbaldehyde compounds. For example, Anderson et.al. (Can. J. Chem. 56, 654-657 (1978)) reacted pyrrole-2-carbonitrile with t-butyl chloride in the presence of aluminum or gallium chloride catalysts, to obtain either 4-t-butyl-pyrrole-2-carbonitrile, or 5-t-butyl-pyrrole-2-carbonitrile. Each of the two isomers of the t-butyl-pyrrole-2-carbonitriles were then reduced to the corresponding aldehydes.

Sources & evidence

ORD record
ord-060e7ec1395b44b6ac1e47b3c5d5cf63
Source dataset
uspto-grants-2002_08
Patent number
US06441194B1

Reaction notes

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