Trifluoroacetic acid → 2-(2-Chloro-5-trifluoromethyl-phenyl)-1H-pyrrole-3-carbonitrile

HRID 924677Notes

Reaction equation

HRID 924677 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=1[C:19]([NH:23][CH2:24][CH:25](OCC)OCC)=[CH:20][C:21]#[N:22]>>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][C:10]=1[C:19]1[NH:23][CH:24]=[CH:25][C:20]=1[C:21]#[N:22]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867205843-[2-Chloro-5-(trifluoromethyl)phenyl]-3-[(2,2-diethoxyethyl)amino]prop-2-enenitrile

Product 1

HCID 709797512-(2-Chloro-5-trifluoromethyl-phenyl)-1H-pyrrole-3-carbonitrileYield 45%

Procedure

To TFA (4 mL) at 5° C. the crude 3-[2-chloro-5-(trifluoromethyl)phenyl]-3-[(2,2-diethoxyethyl)amino]prop-2-enenitrile was added. After stirring at room temperature for 30 min, the reaction mixture was concentrated and then diluted with EtOAc and saturated solution of sodium hydrogen carbonate. The organic layer was separated, washed with water and brine, dried over sodium sulfate and concentrated. Column chromatography on silica gel (0 to 20% EtOAc/hexane) afforded the title compound (584 mg, 45% 2 steps).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiondiluted with EtOAc and saturated solution of sodium hydrogen carbonate
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-106606ee41b243fd8d39e0820643dd19
Source dataset
uspto-grants-2016_03
Patent number
US09283224B2

Reaction notes

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