Methanol → 3-Bromo-4-methoxyaniline

HRID 83713

Reaction equation

HRID 83713 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[O:11][CH3:12].O.O.Cl[Sn]Cl.CO.C([O-])(O)=O.[Na+]>CCOC(C)=O.O>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12]

Participants

7

Reactant 4

HCID 887MethanolHCID 61436Stannous chloride dihydrateHCID 788702-Bromo-4-nitroanisoleHCID 516892Sodium Bicarbonate

Product 1

HCID 9610833-Bromo-4-methoxyanilineYield 92.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-1-methoxy-4-nitrobenzene (2.50 g, 10.8 mmol), SnCl2.2H2O (12.2 g, 53.9 mmol), and MeOH (30 mL) were combined and allowed to stir for 3 h at ambient temperature. To the mixture was added H2O (100 mL) and EtOAc (100 mL) resulting in the formation of a thick emulsion. To this was added sat. aq. NaHCO3 (30 mL). The layers were separated and the aqueous layer was extracted with EtOAc (3×30 mL). The organics were combined and dried over MgSO4 before being filtered. Concentration of the filtrate in vacuo gave 2.02 g of an off-white solid. This material was used without further purification.

Workup

  1. customresulting in the formation of a thick emulsion
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (3×30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationbefore being filtered

Sources & evidence

ORD record
ord-a48eb89408e442eaa73e43e78766a091
Source dataset
uspto-grants-2014_09
Patent number
US08846753B2

Linked notes

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