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

HRID 1673332Notes

Reaction equation

HRID 1673332 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-bromobenzoate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7c5a92a8245349f4a096f4864f0d1190
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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