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

HRID 1600768Notes

Reaction equation

HRID 1600768 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[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]([F:8])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[F:9]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 1375611-Chloro-2,5-difluorobenzene

Product 1

HCID 157514831-Chloro-2,5-difluoro-4-nitrobenzeneYield 85%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a stirred solution of 1-chloro-2,5-difluorobenzene (0.770 g, 5.18 mmol) in concd H2SO4 (8.0 mL) at 0° C., KNO3 (0.525 g, 5.19 mmol) was added in one lot. The resulting yellow 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 residue was dried further under vacuum to afford 0.845 g (85%) of title compound as a yellow liquid; 1H NMR (CDCl3) δ 7.43 (dd, 1 H, J1 =9.6 Hz, J2 =6.0 Hz), 7.93 (t, 1 H, J=7.2 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 residue was dried further under vacuum

Sources & evidence

ORD record
ord-ec036f35fd984ea996539fb3d53ee485
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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