2-Methoxyaniline → 4-Bromo-2-methoxyaniline

HRID 1292832Notes

Reaction equation

HRID 1292832 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[Br:10]Br>C(O)(=O)C>[Br:10][C:8]1[CH:7]=[CH:6][C:4]([NH2:5])=[C:3]([O:2][CH3:1])[CH:9]=1

Participants

4

Reactant 2

HCID 70002-MethoxyanilineHCID 24408Bromine2×

Product 1

HCID 4592574-Bromo-2-methoxyanilineYield 57%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

At room temperature, 3.4 ml (30 mmol, 1.25 eq) of 2-methoxyaniline is diluted in 10 ml of acetic acid. Over approximately 1 hour, 1.2 ml (24 mmol, 0.8 eq) of bromine dissolved in 10 ml of acetic acid is added dropwise. A purple precipitate is formed. When all the bromine has been added, the hydrobromide is filtered on a Buchner funnel and rinsed with acetic acid. Take up the solid in a H2O/CH2Cl2 mixture. A slight excess of KOH pellets is added, the aqueous phase is extracted with CH2Cl2 and the organic phase is dried on MgSO4. Concentration under reduced pressure gives a brown oil which is purified by column chromatography (eluent CH2Cl2). The expected product (3.46 g) is a colorless oil (yield: 57%).

Workup

  1. additionis added dropwise
  2. customA purple precipitate is formed
  3. filtrationthe hydrobromide is filtered on a Buchner funnel
  4. washrinsed with acetic acid
  5. additionA slight excess of KOH pellets is added
  6. extractionthe aqueous phase is extracted with CH2Cl2
  7. customthe organic phase is dried on MgSO4
  8. concentrationConcentration under reduced pressure
  9. customgives a brown oil which
  10. customis purified by column chromatography (eluent CH2Cl2)

Sources & evidence

ORD record
ord-f4b2d52faf654bd1b3a130e6f3763cfc
Source dataset
uspto-grants-2007_07
Patent number
US07238693B2

Reaction notes

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