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

HRID 2064142Notes

Reaction equation

HRID 2064142 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 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

1-Bromo-4-fluoro-2-methylbenzene (10 mmol, 1.89 g) was dissolved in concentrated H2SO4 (sp. gr 1.18) (10 mL) under argon and the mixture cooled to 0° C. KNO3 (10 mmol, 1.01 g) was added portion wise, maintaining the temperature around 0° C. The mixture was then allowed to stir at between 0° C. and 20° C. for 2 h. The reaction mixture was poured into ice and the product extracted with ether (×2). The organic layers were combined, dried (MgSO4) and the solvent removed under reduced pressure to yield the product as an oil (9.4 mmol, 2.2 g, 94%)

Workup

  1. temperaturemaintaining the temperature around 0° C
  2. additionThe reaction mixture was poured into ice
  3. extractionthe product extracted with ether (×2)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-9708a09e85cd4c5d9e1c8893f963a7d2
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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