3-Bromo-1,1,1-trifluoro-2-propanone → 1-Methyl-2-(2-naphthyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile

HRID 653835Notes

Reaction equation

HRID 653835 reaction equation
[CH3:1][NH:2][C:3]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)=[CH:4][C:5]#[N:6].Br[CH2:18][C:19](=O)[C:20]([F:23])([F:22])[F:21]>C1(C)C=CC=CC=1.C(O)(=O)C.C(OCC)(=O)C>[CH3:1][N:2]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:4]([C:5]#[N:6])=[C:3]1[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1

Participants

6

Reactant 2

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 67791408beta-(Methylamino)-2-naphthaleneacrylonitrile

Product 1

HCID 198903041-Methyl-2-(2-naphthyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of β-(methylamino)-2-naphthaleneacrylonitrile (2.5 g, 0.012 mol) in toluene and acetic acid is treated dropwise with 3-bromo-1,1,1-trifluoro-2-propanone (2.3 g, 0.012 mol) at room temperature, heated at reflux temperature for 6 hours, cooled and diluted with ethyl acetate. The organic phase is washed sequentially with water and 5N NaOH, dried (Na2SO4) and concentrated in vacuo to give a brown oil residue. The residue is flash chromatographed (silica gel, hexanes/ethyl acetate, 80/20) to give the title compound as a yellow solid, mp 134° C., identified by mass spectral, IR and NMR analyses.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 6 hours
  3. temperaturecooled
  4. washThe organic phase is washed sequentially with water and 5N NaOH
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customto give a brown oil residue
  8. customchromatographed (silica gel, hexanes/ethyl acetate, 80/20)

Sources & evidence

ORD record
ord-3a3b6d1aa39047efabc8e380c887c679
Source dataset
uspto-grants-1992_07
Patent number
US05128485

Reaction notes

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