Acetic Acid → 5-Amino-2-bromobenzoic acid

HRID 1363403Notes

Reaction equation

HRID 1363403 reaction equation
C(O)(=O)C.[Br:5][C:6]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].C([O-])([O-])=O.[Na+].[Na+]>O.[Fe]>[NH2:15][C:12]1[CH:13]=[CH:14][C:6]([Br:5])=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 2430252-Bromo-5-nitrobenzoic acid

Product 1

HCID 27696245-Amino-2-bromobenzoic acid

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

Glacial acetic acid (75 mL) was added dropwise with stirring, at 40-50° C. to a mixture of compound of example 150 (15 g, 57.62 mmol) and iron dust (15 g, 0.267 mol) in water (120 mL). The reaction mixture was stirred vigorously at 25° C. for 1 h. It was poured into water (200 mL), basified using saturated aqueous Na2CO3 solution and extracted with EtOAc (3×250 mL). The organic extract was washed, dried (anhydrous Na2SO4) and concentrated to obtain 5-amino-2-bromobenzoic acid which was then converted into title compound as follows.

Workup

  1. extractionextracted with EtOAc (3×250 mL)
  2. extractionThe organic extract
  3. washwas washed
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a2a56f483dbe4c76904d35e304bd425c
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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