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

HRID 77010

Reaktionsgleichung

Reaktionsgleichung von HRID 77010
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) is heated under microwave irradiation at 100° C. for 50 minutes. Then 3-fluoroaniline (238 mg, 2.15 mmol) is added again and reaction is heated at 120° C. for 45 minutes in a microwave oven (LC-MS monitoring: complete conversion). The organic solution is diluted with EtOAc and washed with 2N HCl and then with brine. The organic phase is dried over Na2SO4, filtered and the solvent is evaporated to give intermediate I131 as a white solid (510 mg, 90% yield).

Aufarbeitung

  1. customreaction
  2. temperatureis heated at 120° C. for 45 minutes in a microwave oven (LC-MS monitoring: complete conversion)
  3. washwashed with 2N HCl
  4. dry with materialThe organic phase is dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-028285e6183b4505a8eae04ddeb8885b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835682B2

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