Potassium Nitrate → 1-Chloro-4-fluoro-2-methyl-5-nitrobenzene

HRID 1781006Notes

Reaction equation

HRID 1781006 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH3:9].[N+:10]([O-])([O-:12])=[O:11].[K+]>OS(O)(=O)=O>[Cl:1][C:2]1[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]([F:8])=[CH:4][C:3]=1[CH3:9]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 1184752-Chloro-5-fluorotoluene

Product 1

HCID 103524921-Chloro-4-fluoro-2-methyl-5-nitrobenzeneYield 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
28 °C

Procedure

To a stirred solution of 2-chloro-5-fluorotoluene (0.500 g, 3.46 mmol, Lancaster, used as received) in conc. H2SO4 (5.0 mL) at 0° C., KNO3 (0.350 g, 3.46 mmol) was added in one lot. The resulting pale yellow solution was allowed to warm to 28° C. and stirred overnight at 28° C. It was then poured into ice (50 g) and extracted with ether (2×50 mL). The ether was dried over anhydrous Na2SO4, removed under vacuum, and the resulting oil was dried further under vacuum to afford 0.616 g (94%) of the title compound as an oil, which was used as such for the next reaction; 1H NMR (CDCl3): δ2.459 (s, 3H), 7.193 (d, 1H, J1 =11.1 Hz), 8.083 (d, 1H, J1 =6.6 Hz).

Workup

  1. extractionextracted with ether (2×50 mL)
  2. dry with materialThe ether was dried over anhydrous Na2SO4
  3. customremoved under vacuum
  4. customthe resulting oil was dried further under vacuum

Sources & evidence

ORD record
ord-542fdfd736c04d64ac3410cac1f60bbe
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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