Water → Methyl 3-bromo-5-nitrobenzoate

HRID 2208749

Reaktionsgleichung

Reaktionsgleichung von HRID 2208749
[Br:1][C:2]1[C:3](C)=[C:4]([N+:12]([O-:14])=[O:13])[C:5](C)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:16](=O)([O-])[O-].[Na+].[Na+].CI.O>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[C:6]([CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1)[C:7]([O:9][CH3:16])=[O:8]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 86623945Methyl 5-bromo-2-methyl-3-nitrobenzoic acid

Produkt 1

HCID 239341Methyl 3-bromo-5-nitrobenzoateAusbeute 104,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To stirred solution of 5-bromo-2,4-dimethyl-3-nitrobenzoic acid (13 g, 47.44 mmol) in DMF (120 mL), sodium carbonate (15 g, 142.2 mmol) and methyl iodide (4.4 ml, 71.16 mmol) were added. Resulting reaction mass was heated at 60° C. for 8 h. On completion, water was added to the reaction mass and extraction was carried out using ethyl acetate. Combined organic layers were washed with sat. bicarbonate solution and 5 N HCl, dried over sodium sulphate, concentrated under reduced pressure giving desired compound (12.9 g, 86%).

Aufarbeitung

  1. additionwere added
  2. customResulting
  3. customreaction mass
  4. washCombined organic layers were washed with sat. bicarbonate solution and 5 N HCl
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bf978c14db984630b8147a13eb9148b8
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376422B2

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