o-Phenetidine → 4-Bromo-2-ethoxyaniline

HRID 1292834Notes

Reaction equation

HRID 1292834 reaction equation
[Br:1]Br.[CH2:3]([O:5][C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8])[CH3:4].[OH-].[K+]>C(O)(=O)C>[Br:1][C:11]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([O:5][CH2:3][CH3:4])[CH:12]=1

Participants

5

Reactant 3

HCID 7203o-PhenetidineHCID 14797Potassium HydroxideHCID 24408Bromine2×

Product 1

HCID 155555024-Bromo-2-ethoxyanilineYield 59.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Over approximately 1 hour, 3 ml (58.4 mmol) of bromine dissolved in 20 ml of acetic acid is added dropwise to 7.8 ml (60 mmol, 1.03 eq) of 2-ethoxyaniline diluted in 20 ml of acetic acid. When all the bromine has been added, the precipitate formed is filtered on a Buchner funnel and rinsed with acetic acid. The hydrobromide is taken up in H2O, 5 g (90 mmol, 1.5 eq) of KOH pellets is added and extracted with CH2Cl2. The organic phase is dried on MgSO4 and the solvent is evaporated. The residue is purified by column chromatography (eluent CH2Cl2/pentane 9:1) to produce 7.52 g of the expected product as a brown oil (yield: 58%).

Workup

  1. customthe precipitate formed
  2. filtrationis filtered on a Buchner funnel
  3. washrinsed with acetic acid
  4. extractionextracted with CH2Cl2
  5. customThe organic phase is dried on MgSO4
  6. customthe solvent is evaporated
  7. customThe residue is purified by column chromatography (eluent CH2Cl2/pentane 9:1)

Sources & evidence

ORD record
ord-21257b79279149a58b34946a4ac5b056
Source dataset
uspto-grants-2007_07
Patent number
US07238693B2

Reaction notes

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