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

HRID 1600776Notes

Reaction equation

HRID 1600776 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 coned 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) δ 7.17 (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-d6cd0e5768a94f1eb512dd796d1b5371
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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