Methyl trifluoromethyl ketone → 2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

HRID 483626Notes

Reaction equation

HRID 483626 reaction equation
Br[C:2](=[C:5]([NH:13][CH3:14])[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)[C:3]#[N:4].[F:15][C:16]([F:21])([F:20])[C:17](=O)[CH3:18]>C(O)(=O)C.O>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([C:5]2[N:13]([CH3:14])[C:17]([C:16]([F:21])([F:20])[F:15])=[CH:18][C:2]=2[C:3]#[N:4])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 9871Methyl trifluoromethyl ketoneHCID 85317206HCID 85317206, compound

Product 1

HCID 118221892-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of α-bromo-p-chloro-β-(methylamino)cinnamonitrile, (E)- or (Z)- (5.43 g, 0.02 mol) and trifluoroacetone (3.36 g, 2.7 mL, 0.03 mol) in acetic acid is heated at 80° C. for 1-2 hours, heated at 100° C. overnight, diluted with water and extracted with ethyl acetate. The combined organic extracts are washed with water, dried over anhydrous Na2SO4 and concentrated in vacuo to obtain a gum. The gum is flash chromatographed using silica gel and a 15% ethyl acetate in heptane solution to give the title product as a yellow solid (1.7 g, mp 129°-131° C.) which is identified by 1H and 19FNMR spectral analyses.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts are washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto obtain a gum
  6. customchromatographed

Sources & evidence

ORD record
ord-24bf63f06e6342c29ea116e72f44bc86
Source dataset
uspto-grants-1993_07
Patent number
US05225568

Reaction notes

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