Methyl iodide → Methyl 3-iodo-4-methyl-5-nitrobenzoate

HRID 59800

Reaktionsgleichung

Reaktionsgleichung von HRID 59800
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[C:15]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:15][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[C:10]([CH3:11])=[C:2]([I:1])[CH:3]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 596277773-Iodo-4-methyl-5-nitrobenzoic acid

Produkt 1

HCID 24728110Methyl 3-iodo-4-methyl-5-nitrobenzoateAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of 3-iodo-4-methyl-5-nitro-benzoic acid (16.06 g, 52.3 mmol) in acetone (300 mL) was added K2CO3 (14.46 g, 104.6 mmol) followed by methyl iodide ((3.91 mL, 62.76 mmol). The reaction mixture was stirred at 40° C. overnight, then cooled to room temperature and partitioned between ethyl acetate and brine. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure to provide 16.5 g (98%) of 3-iodo-4-methyl-5-nitro-benzoic acid methyl ester.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. custompartitioned between ethyl acetate and brine
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-821743cb204d42a1a8a745aa8aed2a07
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440956B2

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