Ethanol → 4-Bromo-2-ethoxyaniline

HRID 735662Notes

Reaction equation

HRID 735662 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([O:11][CH2:12][CH3:13])[CH:3]=1.CCO.O>[Fe].CC(O)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([O:11][CH2:12][CH3:13])[CH:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 962WaterHCID 155555014-Bromo-2-ethoxy-1-nitrobenzene

Product 1

HCID 155555024-Bromo-2-ethoxyanilineYield 96%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a refluxing solution of 62A (3.0 g, 12.2 mmol), EtOH (60 mL), water (15 mL) and AcOH (10 mL) was added portion-wise Fe powder (5 g, 89.3 mmol) over 30 min. The mixture was heated for 1 h before cooling to ambient temperature and filtering through celite. The filtrate was concentrated in vacuo to afford 62B (2.5 g, 96%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.42 (t, J=7.03 Hz, 3 H) 4.02 (q, J=6.88 Hz, 2 H) 6.57 (d, J=7.91 Hz, 1 H) 6.85-6.90 (m, 2 H).

Workup

  1. temperatureThe mixture was heated for 1 h
  2. filtrationfiltering through celite
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e8d617ded42d43f3b5a936570541d95f
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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