Stannous chloride dihydrate → 4-Bromo-3-fluorobenzene-1,2-diamine

HRID 475226Notes

Reaction equation

HRID 475226 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-])=O)[C:3]=1[F:12].O.O.Cl[Sn]Cl>CCO>[Br:1][C:2]1[C:3]([F:12])=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 27831584-bromo-3-fluoro-2-nitroaniline

Product 1

HCID 27832034-Bromo-3-fluorobenzene-1,2-diamineYield 84.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 140 (34 g, 0.144 mol) and EtOH (510 mL) was added SnCl2.2H2O (130.1 g, 0.576 mol) and the resulting mixture was heated to reflux for 4 h. After the completion of the reaction, the solvent was removed in vacuo. The residue was taken up in water and made slightly basic with 10% NaHCO3. The resulting solid was filtered and washed well with EtOAc. The aqueous layer was separated and extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to afford 25 g (84%) of 4-bromo-3-fluoro-benzene-1,2-diamine (142) as yellow solid which was used without further purification.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 4 h
  3. customAfter the completion of the reaction
  4. customthe solvent was removed in vacuo
  5. filtrationThe resulting solid was filtered
  6. washwashed well with EtOAc
  7. customThe aqueous layer was separated
  8. extractionextracted with EtOAc
  9. dry with materialThe combined organic layers were dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-593ca89e47be4721987adce82fd9c07d
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

Loading…