Stannous Chloride → 3-Bromo-2-fluoroaniline

HRID 877211Notes

Reaction equation

HRID 877211 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[C:4]([N+:8]([O-])=O)[CH:5]=[CH:6][CH:7]=1.[Sn](Cl)Cl>O1CCOCC1.Cl>[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH:5]=[CH:6][CH:7]=1)[NH2:8]

Participants

5

Procedure

Under argon, 1.0 g (4.54 mmol) of 3-bromo-2-fluoronitrobenzene was initially charged in 5 ml of dioxane, and 4.3 g (22.72 mmol) of tin(II) chloride and a few drops of 1 N hydrochloric acid were added. After 2 h of stirring, the reaction mixture was concentrated on a rotary evaporator and the residue was taken up in ethyl acetate. The organic phase was washed with 1 N aqueous sodium hydroxide solution, water and saturated sodium chloride solution and then dried over magnesium sulfate and concentrated. This gave 826 mg (95% of theory) of the title compound.

Workup

  1. concentrationthe reaction mixture was concentrated on a rotary evaporator
  2. washThe organic phase was washed with 1 N aqueous sodium hydroxide solution, water and saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-71bb758042b343c7b9b3b5a5d80e5a3d
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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