Hydrochloric Acid → 2-[(4-Bromo-2-chlorophenyl)amino]-3,4-difluorobenzoic acid

HRID 605669

Reaktionsgleichung

Reaktionsgleichung von HRID 605669
F[C:2]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[C:16]([Cl:21])[CH:15]=1.[NH2-].[Li+].Cl>C(#N)C>[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:2]2[C:10]([F:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[C:16]([Cl:21])[CH:15]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24532Lithium amideHCID 3029322,3,4-Trifluorobenzoic acidHCID 6101694-Bromo-2-chloroaniline

Produkt 1

HCID 594692442-[(4-Bromo-2-chlorophenyl)amino]-3,4-difluorobenzoic acidAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2,3,4-trifluorobenzoic acid (1 g, 5.68 mmol) and 4-bromo-2-chloroaniline (1.2 g, 5.68 mmol) in acetonitrile (10 mL) was added lithium amide (0.39 g, 17.04 mmol) and the reaction stirred at 60° C. for 1.5 hours. The mixture was cooled to room temperature and then to 0° C. and acidified with aq. hydrochloric acid. The obtained precipitate was collected by filtration and washed with cold water and dried in vacuo to afford 2[(4-bromo-2-chlorophenyl)amino]-3,4-difluorobenzoic acid (1.92 g, 94% yield) as a beige solid. MS (EI) for C13H7BrClF2NO2: 363 (MH+).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customto 0° C.
  3. filtrationThe obtained precipitate was collected by filtration
  4. washwashed with cold water
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dd40e3c5df0e4ca0bd816e2ec05a3cf4
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915250B2

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