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

HRID 2191615Notes

Reaction equation

HRID 2191615 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

HCID 58508534Tert-butyl 2-amino-4-bromobenzoateYield 86.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2553bf351ebf41e68b94daa25ffaef4c
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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