Potassium Nitrate → 4-Bromo-5-fluoro-2-nitrotoluene

HRID 1063393Notes

Reaction equation

HRID 1063393 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[F:9].[N+:10]([O-])([O-:12])=[O:11].[K+]>OS(O)(=O)=O>[Br:1][C:2]1[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]([CH3:8])=[CH:4][C:3]=1[F:9]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 5732804-Bromo-3-fluorotoluene

Product 1

HCID 27793654-Bromo-5-fluoro-2-nitrotolueneYield 100%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a stirred solution of 4-bromo-3-fluorotoluene (10 g, 52.9 mmol) in H2SO4 (100 mL) was added KNO3 (5.34 g, 52.9 mmol) at 0° C. After stirring overnight at room temperature, the reaction mixture was poured into ice (200 g) and extracted with EtOAc (3×300 mL). The organic solution was washed with brine (200 mL), dried (Na2SO4), and concentrated to give 12.35 g (100%) of title compound as a pale yellow oil. 1H NMR (CDCl3): 300 MHz δ 8.29 (d, J=6.30 Hz, 1H), 7.12 (d, J=8.61 Hz, 1H), 2.60 (s, 3H).

Workup

  1. extractionextracted with EtOAc (3×300 mL)
  2. washThe organic solution was washed with brine (200 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7a6eb5e9e5104782ba3c8f25ac62a8c5
Source dataset
uspto-grants-2005_11
Patent number
US06964979B2

Reaction notes

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