Sodium Carbonate → 2-Bromo-3-methoxyaniline

HRID 500001Notes

Reaction equation

HRID 500001 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-methoxyaniline

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-Bromo-3-nitroanisole 1b3 (1.00 g; 4.31 mmol) was dissolved in glacial acetic acid (11.0 mL)/ethanol (11.0 mL) and to the solution was added iron powder (0.98 g; 17.5 mmol). The mixture was stirred at reflux for 3.5 hr 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 1b4 (91%; 0.79 g) as a pale yellow oil. MS 201.8 (MH)+; Homogeneity by HPLC (TFA) @ 220 nm: 95%

Workup

  1. temperatureat reflux for 3.5 hr
  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-6cbcc86f79274f7f940ce83d8047af34
Source dataset
uspto-grants-2010_08
Patent number
US07767818B2

Reaction notes

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