Sodium Trifluoroacetate → 1-(4-Methylphenyl)-4-trifluoromethylpyrrole-2-carbonitrile

HRID 248388

Reaction equation

HRID 248388 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:14]#[N:15])[N:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[CH:6]=1.[F:16][C:17]([F:22])([F:21])C([O-])=O.[Na+]>CN1CCCC1=O>[CH3:13][C:10]1[CH:11]=[CH:12][C:7]([N:5]2[CH:6]=[C:2]([C:17]([F:22])([F:21])[F:16])[CH:3]=[C:4]2[C:14]#[N:15])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 517019Sodium TrifluoroacetateHCID 189562501-(4-Methylphenyl)-4-bromo-2-cyanopyrrole

Product 1

HCID 197592701-(4-Methylphenyl)-4-trifluoromethylpyrrole-2-carbonitrileYield 27.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 4-bromo-1-(4-methylphenyl)pyrrole-2-carbonitrile (3.66 g), sodium trifluoroacetate (7.62 g), cuprous iodide (5.34 g) and N-methylpyrrolidone (40 ml) was stirred at 200° C. under a nitrogen atmosphere for 11 hours. The mixture was filtered. The filtrate was poured into water and extracted with ethyl acetate twice. The combined organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography to afford 1-(4-methylphenyl)-4-trifluoromethylpyrrole-2-carbonitrile (0.98 g).

Workup

  1. filtrationThe mixture was filtered
  2. additionThe filtrate was poured into water
  3. extractionextracted with ethyl acetate twice
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5d9592eed04d4b8b9906eed4eb778fa5
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Linked notes

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