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

HRID 1857451Notes

Reaction equation

HRID 1857451 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 90.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a stirred solution of 2-chloro-5-fluorotoluene (10.356 g, 71.628 mmol, Lancaster, used as received) in conc. H2SO4 (70 mL) at 0° C., KNO3 (7.252 g, 71.72 mmol) was added in four equal portions. The resulting pale yellow solution was allowed to warm to room temperature and was stirred overnight at room temperature. It was then poured into ice water (350 g) and extracted with ether (3×100 mL). Ether was dried over anhydrous Na2SO4, removed under vacuum, and the resulting oil was dried further under vacuum to afford 12.277 g (90%) of the title compound as an oil, which was used as such for the next reaction; 1H NMR (CDCl3); δ 2.459 (s, 2H), 7.193 (d, 1H, J1 =11.1 Hz), 8.083 (d, 1H, J1 =6.6 Hz).

Workup

  1. extractionextracted with ether (3×100 mL)
  2. dry with materialEther was dried over anhydrous Na2SO4
  3. customremoved under vacuum
  4. customthe resulting oil was dried further under vacuum

Sources & evidence

ORD record
ord-0b5350c920aa43749aaf7cbe075c00f2
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

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