Stannous chloride dihydrate → 4-Bromo-2,5-difluoroaniline

HRID 1977651Notes

Reaction equation

HRID 1977651 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Br:8])[C:5]([F:9])=[CH:4][C:3]=1[N+:10]([O-])=O.O.O.[Sn](Cl)Cl>CO.Cl>[Br:8][C:6]1[C:5]([F:9])=[CH:4][C:3]([NH2:10])=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 27362864-Bromo-2,5-difluoronitrobenzene

Product 1

HCID 27732854-Bromo-2,5-difluoroaniline

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 2,5-difluoro-4-bromo-nitrobenzene (10 g, 42 mmol) in MeOH (200 mL) and conc. HCl (11 mL) was added tin(II)chloride dihydrate (38 g, 168 mmol) at room temperature. When complete the MeOH was distilled off under vacuum then water and celite were added. The mixture was neutralized with NaOH (50%) and filtered to remove the tin residue. The mixture was extracted with CH2Cl2 and the title compound 468A crystallized from CH2Cl2/hexane.

Workup

  1. distillationWhen complete the MeOH was distilled off under vacuum
  2. additionwater and celite were added
  3. filtrationfiltered
  4. customto remove the tin residue
  5. extractionThe mixture was extracted with CH2Cl2
  6. customthe title compound 468A crystallized from CH2Cl2/hexane

Sources & evidence

ORD record
ord-85fb2605deac41809111c609eb08a1ee
Source dataset
uspto-grants-2001_05
Patent number
US06235740B1

Reaction notes

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