Sodium Carbonate → 2-Bromo-3-methoxyaniline

HRID 547949Notes

Reaction equation

HRID 547949 reaction equation
[Br:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH3:12].C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C.C(O)C.O.[Fe]>[Br:1][C:2]1[C:3]([O:11][CH3:12])=[CH:4][CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

7

Reactant 2

HCID 10340Sodium CarbonateHCID 177502992-Bromo-3-nitroanisole

Product 1

HCID 109105752-Bromo-3-methoxyanilineYield 91%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-Bromo-3-nitroanisole B3 (1.00 g; 4.31 mmol) was dissolved in glacial acetic acid (11.0 mL) and ethanol (11.0 mL). To this solution was added iron powder (0.98 g; 17.5 mmol). The mixture was stirred at reflux for 3.5 h and worked up. The reaction mixture was diluted with water (35 mL), neutralized with solid Na2CO3 and the product extracted with CH2Cl2 (3×50 mL). The extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford the crude product, 2-bromo-3 methoxyaniline B4 (91%; 0.79 g) as a pale yellow oil.

Workup

  1. temperatureat reflux for 3.5 h
  2. extractionthe product extracted with CH2Cl2 (3×50 mL)
  3. dry with materialThe extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3bae056c6df848968c4229d620206867
Source dataset
uspto-grants-2011_05
Patent number
US07939667B2

Reaction notes

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