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

HRID 1781068Notes

Reaction equation

HRID 1781068 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

Procedure

To a stirred solution of 1-chloro-2,4-difluorobenzene (0.829 g, 5.58 mmol) in concd H2SO4 (8.0 mL) at 0° C., KNO3 (0.565 g, 5.59 mmol) was added in one portion. The resulting solution was allowed to warm to room temperature and stirred overnight at room temperature. 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%) pure (1H NMR) title compound as a light red oil; 1H NMR (CDCl3) δ7.17 (dd, 1H, J1 =9.9 Hz, J2 =8.4 Hz), 8.24 (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-e7df90c36ae44d7eb540bd7f7071a5b1
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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