Triethylamine → 3-bromo-4-fluoro-N-(2-fluoro-3-(trifluoromethyl)phenyl)benzamide

HRID 502774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502774
[F:1][C:2]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[F:23])[C:17](Cl)=[O:18].C(N(CC)CC)C>ClCCl>[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[F:23])[C:17]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[C:8]([C:9]([F:10])([F:11])[F:12])[C:2]=1[F:1])=[O:18]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 695983-Bromo-4-fluorobenzoyl chlorideHCID 1455693-Amino-2-fluorobenzotrifluoride

Produkt 1

HCID 594279983-bromo-4-fluoro-N-(2-fluoro-3-(trifluoromethyl)phenyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Fluoro-3-(trifluromethyl)aniline (0.515 g, 0.37 mL, 2.88 mmol) was added to a solution of 3-bromo-4-fluorobenzoyl chloride (0.650 g, 2.74 mmol) in dichloromethane (5 ml), and the mixture stirred at room temperature for 30 min. Triethylamine (0.360 g, 0.50 ml, 3.56 mmol) was added and the solution stirred at room temperature for 1 h. The reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with water, brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a light yellow solid. Trituration with dichloromethane and filtering afforded 3-bromo-4-fluoro-N-(2-fluoro-3-(trifluoromethyl)phenyl)benzamide as a white solid. MS (M−H+) 377.9; Calculated for C14H7BrF5NO: 379.

Aufarbeitung

  1. stirringthe solution stirred at room temperature for 1 h
  2. customThe reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution
  3. customThe aqueous phase was separated
  4. extractionextracted with dichloromethane
  5. washThe combined organic phases were washed with water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a light yellow solid
  10. filtrationTrituration with dichloromethane and filtering

Quellen und Nachweise

ORD-Eintrag
ord-fc826c5bf9d8424d88f2b75831d6b15f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776869B2

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