Stannous Chloride → 2-Chloro-3-fluoroaniline

HRID 2301654Notes

Reaction equation

HRID 2301654 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-])=O.[Sn](Cl)[Cl:13].C([O-])(O)=O.[Na+]>C(O)C>[Cl:13][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:9]

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 183734742-Bromo-1-fluoro-3-nitrobenzene

Product 1

HCID 888842-Chloro-3-fluoroanilineYield 119.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of 2-bromo-3-fluoronitrobenzene (100 mg, 0.46 mmol) in ethanol (5 ml), Tin (II) chloride (520 mg, 2.3 mmol) was added. The reaction mixture was stirred at room temperature for 16 hours. The NaHCO3 (aq) was added to pH=7. Then was extracted with ethyl acetate (3x). The combined organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give desired product (80 mg, 93%). EI-MS m/z 191 (M+).

Workup

  1. extractionThen was extracted with ethyl acetate (3x)
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6ccc7e050b5c4ec69591db5f45e21f80
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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