Nitronium tetrafluoroborate → 2-Bromo-3,4-dimethoxy-6-nitrobenzonitrile

HRID 1582383Notes

Reaction equation

HRID 1582383 reaction equation
[Br:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].F[B-](F)(F)F.[O:19]=[N+:20]=[O:21]>C(#N)C>[Br:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[C:6]([N+:20]([O-:21])=[O:19])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 11073463Nitronium tetrafluoroborateHCID 227212152-Bromo-3,4-dimethoxybenzonitrile

Product 1

HCID 227212172-Bromo-3,4-dimethoxy-6-nitrobenzonitrileYield 85.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-bromo-3,4-dimethoxybenzonitrile (prepared according to step (b), 5.77 g, 23.8 mmol) in acetonitrile (58 ml) at 0° C. was added nitronium tetrafluoroborate (5.67 g, 42.9 mmol) portionwise ensuring that the temperature did not rise above 10° C. After stirring for 4 hours in the range 0° C. to 10° C., the reaction was cautiously quenched into 10% aqueous NaHCO3 (66 ml). The resulting suspension was filtered and the solid dried in vacuo overnight to give 5.83 g of the subtitle product (85%).

Workup

  1. customdid not rise above 10° C
  2. customthe reaction was cautiously quenched into 10% aqueous NaHCO3 (66 ml)
  3. filtrationThe resulting suspension was filtered
  4. customthe solid dried in vacuo overnight

Sources & evidence

ORD record
ord-684d5a538104404fb9da1cdd817793cb
Source dataset
uspto-grants-2004_05
Patent number
US06734303B2

Reaction notes

Loading…