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

HRID 1600722Notes

Reaction equation

HRID 1600722 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-98cfb85baf744a51b1298ba2672f4e27
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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