Potassium Nitrate → 2-Chloro-4-fluoro-5-nitrotoluene

HRID 1600713Notes

Reaction equation

HRID 1600713 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[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]([F:8])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[CH3:9]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 967472-Chloro-4-fluorotoluene

Product 1

HCID 101039792-Chloro-4-fluoro-5-nitrotolueneYield 795.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
28 °C

Procedure

To a stirred solution of 2-chloro-4-fluorotoluene (2.000 g, 1.383 mmol, Aldrich, used as received) in conc. H2SO4 (15.0 mL) at 0° C., KNO3 (1.400 g, 1.385 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 (100 g) and extracted with ethyl acetate (2×100 mL). Ethyl acetate was dried over anhydrous Na2SO4, removed under vacuum, and the resulting oil was dried further under vacuum to afford 2.085 g (80%) of title compound as an oil, which was used as such for the next reaction; 1H NMR (CDCl3): δ 2.422 (s, 3H), 7.325 (d, 1H, J1 =10.2 Hz), 7.973 (d, 1H, J1 =5.2 Hz).

Workup

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

Sources & evidence

ORD record
ord-d54b80d1994d4136bca50548def8954d
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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