Methylamine → HCID 21354507, Verbindung

HRID 63652

Reaktionsgleichung

Reaktionsgleichung von HRID 63652
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([F:9])[CH:3]=1.CC([O-])=O.[K+].[CH3:15][NH2:16]>CN(C=O)C.[Cu]I>[F:9][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[CH3:8])[NH:16][CH3:15]

Komponenten

6

Edukt 3

HCID 6329MethylamineHCID 1710404-Bromo-2-fluorotolueneHCID 517044Potassium Acetate

Produkt 1

HCID 21354507HCID 21354507, VerbindungAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a suspension of 4-bromo-2-fluoro-1-methylbenzene (1.0 g, 5.3 mmol), KOAc (1.3 g, 13.2 mmol), and CuI (1.2 g, 6.4 mmol) in DMF (20 mL) was added methylamine (26.5 mL, 2.0M in THF, 53.0 mmol) at r.t. under N2. The reaction was stirred at 100° C. overnight in a sealed tube. The reaction mixture was filtered, diluted with water (50 mL), and extracted with EtOAc (50 mL×3). The organic layers were washed with ammonium hydroxide (50 mL×3) and brine (50 mL), dried (Na2SO4), and concentrated. The residue was purified by silica gel chromatography (PE:EtOAc=20:1) to give 310 mg (42%) of the title compound as a yellow oil. [M+H] Calc'd for C8H10FN, 140. Found, 140.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. additiondiluted with water (50 mL)
  3. extractionextracted with EtOAc (50 mL×3)
  4. washThe organic layers were washed with ammonium hydroxide (50 mL×3) and brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (PE:EtOAc=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-d9c8422db28a4c06a2709eddfc0e6b3a
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447046B2

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