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

HRID 1673332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1673332
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-bromobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3.0 g of iron powder was added to a mixed solution of 28 mL of methanol and 28 mL of acetic acid containing 5.5 g of tert-butyl 4-bromo-2-nitrobenzoate, and the resulting mixture was heated to reflux for 1 hour. After one reaction mixture was cooled to room temperature, a saturated sodium hydrogen carbonate aqueous solution and ethyl acetate were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure to obtain 4.3 g of tert-butyl 2-amino-4-bromobenzoate as pale yellow oil.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 1 hour
  3. customAfter one reaction mixture
  4. custominsoluble were removed by filtration
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. washafter washed with a saturated sodium hydrogen carbonate aqueous solution
  8. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7c5a92a8245349f4a096f4864f0d1190
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07999132B2

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