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

HRID 1600730Notes

Reaction equation

HRID 1600730 reaction equation
[Cl: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>[Cl: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 1370011-Chloro-2,4-difluorobenzene

Product 1

HCID 738671-Chloro-2,4-difluoro-5-nitrobenzene

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
28 °C

Procedure

To a stirred solution of 1chloro-2,4-difluorobenzene (0.829 g, 5.58 mmol, Aldrich, used as received) in conc. H2SO4 (8.0 mL) at 0° C., KNO3 (0.565 g, 5.59 mmol) was added in one lot. The resulting solution was allowed to warm to 28° C. and stirred overnight at 28° C. It was then poured into ice (80 g) and extracted with ethyl acetate (75 mL). The ethyl acetate was dried over anhydrous Na2SO4, removed under vacuum, and the resulting oil was dried further under vacuum to afford 1.007 g (93%) of the pure (1H NMR) title compound as a light red oil; 1H NMR (CDCl3): δ 7.168 (dd, 1H, J1 =9.9 Hz, J2 =8.4 Hz), 8.238 (t, 1H, J=7.5 Hz).

Workup

  1. extractionextracted with ethyl acetate (75 mL)
  2. dry with materialThe ethyl acetate was dried over anhydrous Na2SO4
  3. customremoved under vacuum
  4. customthe resulting oil was dried further under vacuum

Sources & evidence

ORD record
ord-f60b7810d537432296c1f89e93e83082
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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