Acetonitrile → 4-Bromo-2,3-difluoroaniline

HRID 2092529Notes

Reaction equation

HRID 2092529 reaction equation
[F:1][C:2]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C(#N)C.[Br-:13].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>O>[Br:13][C:7]1[CH:6]=[CH:5][C:3]([NH2:4])=[C:2]([F:1])[C:8]=1[F:9]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 782782,3-DifluoroanilineHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 146210374-Bromo-2,3-difluoroanilineYield 34.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure for preparing this compound was based on that described in International Patent Publication No. WO 2010/091272. To a 100 mL round bottom flask, 2,3-difluoroaniline (1 g, 0.0077 mol) and ACN (30 mL) were added. To the flask was added the solution of tetrabutylammonium tribromide (3.71 g, 0.0077 mol, in 10 mL of ACN). The reaction mixture was stirred at room temperature for 3 h. The reaction mass was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with brine and evaporated under reduced pressure to get the crude product. The crude product was purified by column chromatography using 60-12 silica gel and 30% ethyl acetate in hexane to get the title compound [0.55 g, 34%]. The obtained product was immediately taken to the next step.

Workup

  1. customThe procedure for preparing this compound
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with brine
  4. customevaporated under reduced pressure
  5. customto get the crude product
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-0537dde571694b46b4b0b47ab973ad5b
Source dataset
uspto-grants-2013_05
Patent number
US08440662B2

Reaction notes

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