2-Fluoroaniline → Methyl 2-fluoro-4-[(2-fluoroanilino)methyl]benzoate

HRID 1497985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497985
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([F:27])[CH:18]=1>CN(C=O)C>[F:27][C:19]1[CH:18]=[C:17]([CH2:16][NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[F:1])[CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22]

Komponenten

5

Edukt 3

HCID 95842-FluoroanilineHCID 11430Potassium CarbonateHCID 18759821methyl 4-(bromomethyl)-2-fluorobenzoate

Produkt 1

HCID 86720707Methyl 2-fluoro-4-[(2-fluoroanilino)methyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a mixture of 2-fluoroaniline (0.12 mL, 1.2 mmol) and potassium carbonate (207 mg, 1.5 mL) in DMF (5 mL) was added methyl 4-(bromomethyl)-2-fluoro-benzoate (247 mg, 1 mmol). The mixture was heated to 60° C. for 18 hours. The solvent was removed in vacuo. The mixture was partitioned between DCM (15 mL) and water (15 mL), the layers were separated and the organic phase was passed through a hydrophobic fit. The solvent was removed in vacuo and the residue was used directly in the next step without any further purification. LCMS (Method 2): [MH+]=278 at 3.60 min.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customThe mixture was partitioned between DCM (15 mL) and water (15 mL)
  3. customthe layers were separated
  4. customThe solvent was removed in vacuo
  5. customthe residue was used directly in the next step without any further purification
  6. customat 3.60 min.

Quellen und Nachweise

ORD-Eintrag
ord-ba4959fc871946ae8949319b0885d9c1
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199980B2

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