Acetic Acid → Tert-butyl 2-amino-4-bromobenzoate

HRID 2191615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2191615
CO.C(O)(=O)C.[Br:7][C:8]1[CH:20]=[CH:19][C:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[C:10]([N+:21]([O-])=O)[CH:9]=1.C(=O)([O-])O.[Na+]>[Fe].C(OCC)(=O)C>[NH2:21][C:10]1[CH:9]=[C:8]([Br:7])[CH:20]=[CH:19][C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 26369829tert-Butyl 4-bromo-2-nitrobenzoate

Produkt 1

HCID 58508534Tert-butyl 2-amino-4-bromobenzoateAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Iron powder 3.0 g were added to a mixed solution methanol 28 mL and acetic acid 28 mL of tert-butyl 4-bromo-2-nitrobenzoate 5.5 g, it was heated and refluxed for 1 hour. After the reaction mixture was cooled to room temperature, saturated sodium hydrogen carbonate aqueous solution and ethyl acetate were added to it, and insoluble matter was filtrated. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution, the solvent was removed under reduced pressure to give tert-butyl 2-amino-4-bromobenzoate 4.3 g of pale yellow oil.

Aufarbeitung

  1. temperaturewas heated
  2. temperaturerefluxed for 1 hour
  3. filtrationwas filtrated
  4. customThe organic layer was separated
  5. washafter sequential washing with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution
  6. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2553bf351ebf41e68b94daa25ffaef4c
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08327467B2

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