Water → 2-Bromo-5-chloroaniline

HRID 2224307Notes

Reaction equation

HRID 2224307 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-])=O.Cl[Sn]Cl.O.C([O-])(O)=O.[Na+]>CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH2:9]

Participants

6

Reactant 4

HCID 962WaterHCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 27949042-Bromo-5-chloronitrobenzene

Product 1

HCID 113102762-Bromo-5-chloroanilineYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-bromo-4-chloro-2-nitro-benzene (10.0 g, 42.3 mmol) and SnCl2 (24.0 g, 127 mmol) in EtOAc (100 mL) was heated to reflux for 1 hour. After cooling to room temperature, water and NaHCO3 were added slowly at 0° C. until the reaction was basic. The mixture was filtered through celite and rinsed with EtOAc. The filtrate was washed with aqueous NaHCO3 solution and brine, dried (MgSO4), filtered and concentrated to give 6A (8.7 g, 100%) as black crystals. Rt=2.489 min.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. filtrationThe mixture was filtered through celite
  4. washrinsed with EtOAc
  5. washThe filtrate was washed with aqueous NaHCO3 solution and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b552eeadc5b74c3582e4b8e985834225
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Reaction notes

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