4-Fluoro-2-(trifluoromethyl)aniline → HCID 178471926, compound

HRID 2104507Notes

Reaction equation

HRID 2104507 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.[CH2:13]([O:15][C:16](=[O:30])[C:17]([C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:18]OCC)[CH3:14]>C1(C)C=CC=CC=1>[CH2:13]([O:15][C:16](=[O:30])[C:17]([C:22](=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[CH:18][NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][C:4]=1[C:9]([F:10])([F:11])[F:12])[CH3:14]

Participants

4

Reactant 2

HCID 678534-Fluoro-2-(trifluoromethyl)anilineHCID 98006Ethyl 2-benzoyl-3-ethoxyacrylate

Product 1

HCID 178471926HCID 178471926, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-fluoro-2-trifluoromethyl-aniline (5.0 g, 27.89 mmol) and 2-benzoyl-3-ethoxy-acrylic acid ethyl ester (6.9 g, 27.89 mmol) in toluene (125 mL) was heated at reflux. After 18 hr, the reaction was cooled, concentrated and purified by column chromatography (eluent 10% to 40% Et2O/hexanes) to give 2-benzoyl-3-(2-trifluoromethyl-4-fluoro-phenylamino)-acrylic acid ethyl ester (6.6 g, 62%); MS (ESI) m/z 382 (M+H)+; 1H NMR E:Z (mixture 1:1) (CDCl3): δ 0.88 (t, J=5.38 Hz, 3H), 0.95 (t, J=5.38 Hz, 3H), 4.02 (q, J=5.38 Hz, 2H), 4.07 (t, J=5.38 Hz, 2H), 7.29-7.51 (m, 10H), 7.53-7.56 (dt, J=9.67, 1.54 Hz, 2H), 7.66-7.68 (dt, J=8.33, 1.41 Hz, 2H), 8.10-8.13 (d, J=12.68 Hz, 2H), 8.36-8.39 (d, J=12.43 Hz, 2H), 11.17-11.20 (d, J=12.68 Hz, 1H), 12.39-12.42 (d, J=12.43 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperaturethe reaction was cooled
  4. concentrationconcentrated
  5. custompurified by column chromatography (eluent 10% to 40% Et2O/hexanes)

Sources & evidence

ORD record
ord-3f3c5134b7484192a62894d11c6dc1f1
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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