Trifluoroacetic acid → 5-(2,5-difluorophenyl)-3,4-dihydro-2H-pyrrole

HRID 1054434Notes

Reaction equation

HRID 1054434 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[C:16]1[N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18][CH:17]=1>C(Cl)Cl.CCOC(C)=O>[F:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[C:16]1[CH2:17][CH2:18][CH2:19][N:20]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89618599HCID 89618599, compound

Product 1

HCID 583357265-(2,5-difluorophenyl)-3,4-dihydro-2H-pyrroleYield 83.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

TFA (108 g, 940 mmol) was added to a solution of tert-butyl 5-(2,5-difluorophenyl)-2,3-dihydro-1H-pyrrole-1-carboxylate (53 g, 188 mmol) in DCM (300 mL) at 0° C. and stirring was continued at 20-35° C. for 2 h. The reaction mixture was concentrated under reduced pressure to afford the crude, which was diluted with EtOAc, washed with saturated NaHCO3 solution, dried over anhydrous sodium sulphate to afford 28.5 g of the title compound. MS (ESI): m/z 181.9 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto afford the crude, which
  3. washwashed with saturated NaHCO3 solution
  4. dry with materialdried over anhydrous sodium sulphate

Sources & evidence

ORD record
ord-d81f0e754fec4b9e8340c87021d6b72c
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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