2-Bromo-5-fluorotoluene → 1-Bromo-4-fluoro-2-methyl-5-nitrobenzene

HRID 1055640Notes

Reaction equation

HRID 1055640 reaction equation
F[B-](F)(F)F.[O:6]=[N+:7]=[O:8].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[CH3:17]>ClCCl>[Br:9][C:10]1[CH:15]=[C:14]([N+:7]([O-:8])=[O:6])[C:13]([F:16])=[CH:12][C:11]=1[CH3:17]

Participants

4

Reactant 2

HCID 967432-Bromo-5-fluorotolueneHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 100369831-Bromo-4-fluoro-2-methyl-5-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.21 g (16.7 mmol) of nitronium tetrafluoroborate were suspended in 30 ml of dichloromethane. A solution of 3.0 g (15.9 mmol) of 2-bromo-5-fluorotoluene in 30 ml of dichloromethane was added dropwise under reflux. The mixture was then stirred under reflux for another 6 h. The mixture was then poured onto ice and extracted with dichloromethane, and the organic phase was washed with water, dried over sodium sulphate and concentrated on a rotary evaporator. This gave a yellow oil which formed crystals overnight. These were separated off, washed with 2 ml of pentane and dried. This gave 265 mg (6.9% of theory) of the title compound.

Workup

  1. temperatureunder reflux
  2. temperatureunder reflux for another 6 h
  3. additionThe mixture was then poured onto ice
  4. extractionextracted with dichloromethane
  5. washthe organic phase was washed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated on a rotary evaporator
  8. customThis gave a yellow oil which
  9. customformed crystals overnight
  10. customThese were separated off
  11. washwashed with 2 ml of pentane
  12. customdried

Sources & evidence

ORD record
ord-d5d527ad60a74a17b4b005abab1d608f
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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