Hydrochloric Acid → 5-Bromo-2-methoxyaniline

HRID 380438Notes

Reaction equation

HRID 380438 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-a0c2b77fab6141fd9451f555a8d1450e
Source dataset
uspto-grants-2001_10
Patent number
US06303600B1

Reaction notes

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