N-bromobutanimide → 3-Bromo-2,6-difluorobenzonitrile

HRID 2173236Notes

Reaction equation

HRID 2173236 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[C:4]#[N:5].C1C(=O)N([Br:18])C(=O)C1>S(=O)(=O)(O)O>[Br:18][C:7]1[C:6]([F:10])=[C:3]([C:2]([F:1])=[CH:9][CH:8]=1)[C:4]#[N:5]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 566047073-Bromo-2,6-difluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of compound 2,6-difluorobenzonitrile (5 g, 36 mmol) in concentrated sulfuric acid (25 mL) was added with NBS (7 g, 39.6 mmol) at 0° C. and stirred at ambient temperature for 2 days. Ice was added to the reaction solution. The mixture was extracted with EtOAc. The organic layer was washed with water, saturated NaHCO3 solution, brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified with fast column chromatograph to give compound 3-bromo-2,6-difluorobenzonitrile. 1H-NMR (400 MHz, CDCl3) δ ppm 7.78˜7.83 (m, 1H), 6.98˜7.03 (m, 1H).

Workup

  1. additionIce was added to the reaction solution
  2. extractionThe mixture was extracted with EtOAc
  3. washThe organic layer was washed with water, saturated NaHCO3 solution, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified with fast column chromatograph

Sources & evidence

ORD record
ord-c365ae0707414b11a737e0feea7c5b38
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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