Hydrochloric Acid → 5-Bromo-2-methoxyaniline

HRID 1166237Notes

Reaction equation

HRID 1166237 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1.Cl>C(O)C.[Fe]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([NH2:10])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 1185334-Bromo-2-nitroanisole

Product 1

HCID 35853285-Bromo-2-methoxyanilineYield 82%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Iron powder (16.1 g) was added to a stirring mixture of 4-bromo-2-nitroanisole (13.92 g, 60 mmol) in 200 ml ethanol. The reaction mixture was heated to reflux, whereupon 50 ml of 0.5N HCl solution was added dropwise over a 45 minute period. The reaction mixture was then refluxed for an additional 3 hours then was allowed to cool to room temperature and was then filtered through celite and the resulting filtrate was concentrated under vacuum. The resulting solid was suspended in saturated NaHCO3 solution, then collected by filtration, and washed with water. The solid was recrystallized from cyclohexane to yield 4-bromo-2-aminoanisole (9.90 g, 82%). m.p. 93° C.; 1H NMR (300 MHz, CDCl3) δ6.69 (2H, m), 6.52 (1H, d, J=9.0 Hz), 3.72 (3H, s).

Workup

  1. temperatureThe reaction mixture was heated
  2. additionwas added dropwise over a 45 minute period
  3. temperatureThe reaction mixture was then refluxed for an additional 3 hours
  4. filtrationwas then filtered through celite
  5. concentrationthe resulting filtrate was concentrated under vacuum
  6. filtrationcollected by filtration
  7. washwashed with water
  8. customThe solid was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-53f76fb600244d1abf79ab0d8743f69a
Source dataset
uspto-grants-2003_09
Patent number
US06613786B2

Reaction notes

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