Methyl iodide → Benzoic acid, 2-bromo-5-fluoro-, methyl ester

HRID 715995

Reaktionsgleichung

Reaktionsgleichung von HRID 715995
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH3:12][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:2]=1[Br:1]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27781812-Bromo-5-fluorobenzoic acid

Produkt 1

HCID 138875Benzoic acid, 2-bromo-5-fluoro-, methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-5-fluorobenzoic acid (7.92 g, 36.2 mmol) in N,N-dimethylformamide (75 mL) was added potassium carbonate (6.91 g, 50.0 mmol) as a solid in one portion at room temperature. The mixture was stirred for 5 minutes and iodomethane (6.39 g, 45.0 mmol) was added in one portion. The mixture was stirred at ambient temperature for 22 hours. The reaction mixture was partitioned between ethyl acetate and water. The aqueous portion was extracted with additional ethyl acetate (3×) and the combined organic extracts were washed successively with 10% potassium carbonate solution, water and brine. The organic portion was dried (Na2SO4) and concentrated to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.87 (s, 3H) 7.41 (td, J=8.56, 3.22 Hz, 1H) 7.65 (dd, J=8.99, 3.22 Hz, 1H) 7.81 (dd, J=9.16, 5.09 Hz, 1H); MS (+DCI/NH3) m/z 250.0 [M+NH4]+.

Aufarbeitung

  1. stirringThe mixture was stirred at ambient temperature for 22 hours
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. extractionThe aqueous portion was extracted with additional ethyl acetate (3×)
  4. washthe combined organic extracts were washed successively with 10% potassium carbonate solution, water and brine
  5. dry with materialThe organic portion was dried (Na2SO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ac1d53a953ad4ed1886735e23de1b7a4
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187483B2

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