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

HRID 53810

Reaction equation

HRID 53810 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); δ 7.141 (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-5b65582b6713465381b61a73f53f9b59
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Linked notes

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