Potassium Nitrate → 1-Bromo-2,4-difluoro-5-nitrobenzene

HRID 439531Notes

Reaction equation

HRID 439531 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[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]([N+:10]([O-:12])=[O:11])[C:5]([F:8])=[CH:4][C:3]=1[F:9]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 676741-Bromo-2,4-difluorobenzene

Product 1

HCID 2230781-Bromo-2,4-difluoro-5-nitrobenzeneYield 91.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
28 °C

Procedure

To a stirred solution of 1-bromo-2,4-difluorobenzene (0.512 g, 2.65 mmol, Aldrich, used as received) in conc. H2SO4 (5.0 mL) at 0° C., KNO3 (0.275 g, 2.72 mmol) was added in one portion. The resulting solution was allowed to warm to 28° C. and was stirred at that temperature overnight. It was then poured into ice (50 g) and extracted with ethylacetate (50 mL). The extract was dried over Na2SO4, and evaporated to afford 0.576 g (91%) pure title compound as light red oil; 1H NMR (CDCl3); δ7.141 (dd, 1H, J1 10.2 Hz, J2 =7.8 Hz), 8.375 (t, 1H, J=7.5 Hz).

Workup

  1. extractionextracted with ethylacetate (50 mL)
  2. dry with materialThe extract was dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-745959f1cc00461f8b1ed9db387be198
Source dataset
uspto-grants-1996_05
Patent number
US05514680

Reaction notes

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