Hydrochloric Acid → 3-Bromo-4-chloroaniline

HRID 377020Notes

Reaction equation

HRID 377020 reaction equation
O.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[Br:13].[OH-].[Na+]>C(O)C.[Fe]>[Br:13][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][C:4]=1[Cl:3])[NH2:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 27355492-Bromo-1-chloro-4-nitrobenzene

Product 1

HCID 128437223-Bromo-4-chloroaniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

A mixture of iron (17.9 g), ethanol (120 ml), water (80 ml) and conc. hydrochloric acid (1.5 ml) was heated to 70° C., this temperature was maintained during the addition of 1-chloro-2-bromo-4-nitrobenzene (21.0 g) in ethanol (100 ml) over 25 min. The mixture was heated to reflux for 11/4 hours before adjusting the pH to 9-10 with sodium hydroxide solution. The mixture was filtered hot through Hyflo™ washing with hot ethanol and water. The mixture was concentrated, dichloromethane added and the organic solution washed with water then dried (MgSO4). The product was purifed by silica gel chromatography then recrystalised from ether/hexane to give the sub-title compound as a solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 11/4 hours
  3. filtrationThe mixture was filtered hot through Hyflo™
  4. washwashing with hot ethanol and water
  5. concentrationThe mixture was concentrated
  6. additiondichloromethane added
  7. washthe organic solution washed with water
  8. dry with materialthen dried (MgSO4)
  9. customthen recrystalised from ether/hexane

Sources & evidence

ORD record
ord-ea4d21fcbc47417bb1e3e6e30af50085
Source dataset
uspto-grants-2000_02
Patent number
US06022976

Reaction notes

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