Potassium Nitrate → 4-Bromo-2,5-difluoronitrobenzene

HRID 1857395Notes

Reaction equation

HRID 1857395 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[F:9].[N+:10]([O-])([O-:12])=[O:11].[K+]>OS(O)(=O)=O>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[F:9]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 678622-Bromo-1,4-difluorobenzene

Product 1

HCID 27362864-Bromo-2,5-difluoronitrobenzeneYield 89.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
28 °C

Procedure

To a stirred solution of 1-bromo-2,5-difluorobenzene (1.000 g, 5.181 mmol, Aldrich, used as received) in conc. H2SO4 (8.0 mL) at 0° C., KNO3 (0.525 g, 5.19 mmol) was added in one lot. The resulting yellow solution was allowed to warm to 28° C. and stirred at 28° C. overnight. It was then poured into ice (80 g) and extracted with ethyl acetate (75 mL). The ethyl acetate was dried over anhydrous Na2SO4, removed under vacuum, and the resulting white solid was dried further under vacuum to afford 1.102 g (89%) of the title compound as a white powder; m.p. 58-60° C.; 1H NMR (CDCl3): δ 7.591 (dd, 1H, J1 =9.6 Hz, J2 =5.4 Hz), 7.891 (t, 1H, J=6.9 Hz).

Workup

  1. extractionextracted with ethyl acetate (75 mL)
  2. dry with materialThe ethyl acetate was dried over anhydrous Na2SO4
  3. customremoved under vacuum
  4. customthe resulting white solid was dried further under vacuum

Sources & evidence

ORD record
ord-e225dcd807cf4516a062cc4413ceee4f
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

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