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

HRID 1068654Notes

Reaction equation

HRID 1068654 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 warn 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) δ 7.17 (dd, 1H, J1=9.9 Hz, J2=8.4 Hz), 8.24 (t, 1H, J=7.5 Hz).

Workup

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

Sources & evidence

ORD record
ord-cf1d413f91ee438ea3139184cfbe1cac
Source dataset
uspto-grants-2001_06
Patent number
US06251903B1

Reaction notes

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