Sulfuric Acid → 4-Bromo-5-fluoro-2-nitrotoluene

HRID 2227479Notes

Reaction equation

HRID 2227479 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[Br:12]Br.S(=O)(=O)(O)O>[N+]([O-])([O-])=O.[Ag+]>[Br:12][C:3]1[C:2]([F:1])=[CH:7][C:6]([CH3:8])=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 24408BromineHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 27793654-Bromo-5-fluoro-2-nitrotoluene

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Procedure

A mixture of 5-fluoro-2-nitrotoluene (1.00 g), silver nitrate (2.21 g), bromine (0.37 ml) and conc. sulfuric acid (6 ml) was stirred for 1 hour under cooling with ice. The reaction mixture was added dropwise to ice water and then subjected to extraction with chloroform. The organic layer was washed with saturated sodium hydrogencarbonate solution, dried with anhydrous magnesium sulfate and then concentrated at reduced pressure to give the titled compound in admixture with its regioisomer at a ratio of 5:3 (yield, 83%).

Workup

  1. temperatureunder cooling with ice
  2. extractionsubjected to extraction with chloroform
  3. washThe organic layer was washed with saturated sodium hydrogencarbonate solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-98cdda961bc84f9083d49879a8cbb7d7
Source dataset
uspto-grants-2002_07
Patent number
US06414005B1

Reaction notes

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