Trifluoroacetic acid → Trifluoroacetic acid

HRID 2054741Notes

Reaction equation

HRID 2054741 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[C:16]1[CH2:20][N:19](C(OC(C)(C)C)=O)[CH:18]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:17]=1>ClCCl>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[C:16]1[CH2:20][NH:19][CH:18]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:17]=1.[C:3]([OH:5])([C:2]([F:7])([F:6])[F:1])=[O:4]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59656605tert-butyl 4-(2-chloro-5-fluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

Product 2

HCID 6422Trifluoroacetic acidHCID 596566114-(2-chloro-5-fluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (10 mL) was added to a solution of tert-butyl 4-(2-chloro-5-fluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate (14, 320 mg, 0.856 mmol, 1 equiv) in dichloromethane (40 mL) at 23° C., and the resulting mixture was stirred for 30 min, then concentrated to give 4-(2-chloro-5-fluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole (1-5) as a TFA salt (brown oil). LRMS m/z (M+H) 274.1 found, 274.1 required.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-914e16f5bd18423e98934255c8858a02
Source dataset
uspto-grants-2008_02
Patent number
US07329762B2

Reaction notes

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