3-Bromo-4-ethylaniline → 3-Bromo-4-ethylphenol

HRID 584300Notes

Reaction equation

HRID 584300 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](N)[CH:5]=[CH:6][C:7]=1[CH2:8][CH3:9].N([O-])=[O:12].[Na+]>>[Br:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[CH:6][C:7]=1[CH2:8][CH3:9]

Participants

3

Reactant 2

HCID 223456173-Bromo-4-ethylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 223455883-Bromo-4-ethylphenol

Procedure

In a manner similar to that of Example 1(d), by reacting 27 g (135 mmol) of 3-bromo-4-ethylphenylamine with 11 g (162 mmol) of sodium nitrite, and after purification by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (90/10), 13 g (49%) of the expected product are obtained in the form of a brown oil.

Workup

  1. customafter purification by chromatography on a column of silica
  2. washeluted with a mixture of heptane and ethyl acetate (90/10), 13 g (49%) of the expected product
  3. customare obtained in the form of a brown oil

Sources & evidence

ORD record
ord-e01dc76730c741868cac98fbfe867c85
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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