Potassium Nitrate → 1-Bromo-4-fluoro-2-methyl-5-nitrobenzene

HRID 1857400Notes

Reaction equation

HRID 1857400 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH3:9].[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]([F:8])=[CH:4][C:3]=1[CH3:9]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 967432-Bromo-5-fluorotoluene

Product 1

HCID 100369831-Bromo-4-fluoro-2-methyl-5-nitrobenzeneYield 99%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
28 °C

Procedure

To a stirred solution of 2-bromo-5-fluorotoluene (1.495 g, 7.909 mmol, Aldrich, used as received) in conc. H2SO4 (10.0 mL) at 0° C., KNO3 (0.800 g, 7.91 mmol) was added in one lot. The resulting pale yellow solution was warmed to 28° C. and stirred overnight at 28° C. It was then poured into ice (50 g) and extracted with ethyl acetate (75 mL). The ethyl acetate was dried over anhydrous Na2SO4, removed under vacuum, and the resulting oil dried further under vacuum to afford 1.832 g (98%) of the title compound as an oil; 1H NMR (CDCl3): δ 2.495 (s, 33H), 7.213 (d, 1H, J1 =11.4 Hz), 8.268 (d, 1H, J1 =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 resulting oil dried further under vacuum

Sources & evidence

ORD record
ord-6ddc1569c0f64bdba0341e62cb4b9a2e
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

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