3-Fluoroaniline → (4-Fluoro-phenyl)-(3-fluoro-phenylamino)-acetic acid

HRID 1044033

Reaktionsgleichung

Reaktionsgleichung von HRID 1044033
Br[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[F:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17]>C(#N)C.CCOC(C)=O>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH:2]([NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:14]([F:13])[CH:15]=2)[C:3]([OH:5])=[O:4])=[CH:7][CH:8]=1

Komponenten

5

Edukt 2

HCID 97423-Fluoroaniline2×HCID 16217752Bromo(4-fluorophenyl)acetic acid

Produkt 1

HCID 54890833(4-Fluoro-phenyl)-(3-fluoro-phenylamino)-acetic acidAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-bromo-2-(4-fluorophenyl)acetic acid (500 mg, 2.15 mmol) and 3-fluoroaniline (477 mg, 4.29 mmol) in acetonitrile (8 ml) was heated under microwave irradiation at 100° C. for 50 minutes. Then 3-fluoroaniline (238 mg, 2.15 mmol) was added again, and the reaction mixture was heated at 120° C. for 45 minutes in a microwave oven (UPLC-MS monitoring: complete conversion). The organic solution was diluted with EtOAc and was washed with 2N HCl and then with brine. The organic phase was dried over Na2SO4, filtered and the solvent was evaporated to give 2-(4-fluorophenyl)-2-(3-fluorophenylamino)acetic acid (510 mg, 90% yield).

Aufarbeitung

  1. temperaturethe reaction mixture was heated at 120° C. for 45 minutes in a microwave oven (UPLC-MS monitoring: complete conversion)
  2. washwas washed with 2N HCl
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-00e485c4da9d42d0b1ddd573c2dd10c1
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563577B2

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