Hydrochloric Acid → 5-Bromo-2-methoxyaniline

HRID 392225Notes

Reaction equation

HRID 392225 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]([CH:3]=1)[NH2:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 1185334-Bromo-2-nitroanisole

Product 1

HCID 35853285-Bromo-2-methoxyanilineYield 72.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A stirred mixture of 4-bromo-2-nitroanisole (98.56 g) and iron powder (113.7 g) in ethanol (1.51) was heated to reflux and treated dropwise with hydrochloric acid (350 ml, 0.5N) over 1 hour. After refluxing for a further 3 hours the reaction mixture was cooled to room temperature then filtered through hyflosupercel. The filtrate was evaporated and the residue was treated with saturated sodium bicarbonate solution (21) then filtered. The solid was washed with water then recrystallised from cyclohexane to give the title compound (61.98 g) as a pale brown solid, m.p. 93-93° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureAfter refluxing for a further 3 hours the reaction mixture
  4. filtrationthen filtered through hyflosupercel
  5. customThe filtrate was evaporated
  6. additionthe residue was treated with saturated sodium bicarbonate solution (21)
  7. filtrationthen filtered
  8. washThe solid was washed with water
  9. customthen recrystallised from cyclohexane

Sources & evidence

ORD record
ord-ba04c4b7f37f4d718fc1dfbf518c086f
Source dataset
uspto-grants-2004_10
Patent number
US06800645B1

Reaction notes

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