Sulfuric Acid → 1-Bromo-4-fluoro-2-methyl-3-nitrobenzene

HRID 1771650Notes

Reaction equation

HRID 1771650 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N+:9]([O-:11])=[O:10].OS(O)(=O)=O.C1C(=O)N([Br:24])C(=O)C1>C(O)(C(F)(F)F)=O>[Br:24][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([N+:9]([O-:11])=[O:10])[C:4]=1[CH3:8]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 67184N-bromobutanimideHCID 197738031-Fluoro-3-methyl-2-nitrobenzene

Product 1

HCID 585404001-Bromo-4-fluoro-2-methyl-3-nitrobenzeneYield 67%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 1-fluoro-3-methyl-2-nitro-benzene (5 g, 32.24 mmol, 1.0 eq) in TFA (25 mL) and conc.H2SO4 (10 mL) at 0° C. was added NBS (6.31 g, 35.46 mmol, 1.1 eq) in portions. After addition, the mixture was stirred at room temperature for 2 h. The resulting mixture was poured onto ice and the precipitate that formed collected by filtration, washed with water and dried in vacuo to give the title compound as a yellow solid (5 g, 67%).

Workup

  1. additionAfter addition
  2. additionThe resulting mixture was poured onto ice
  3. customthe precipitate that formed
  4. filtrationcollected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e59d487442eb4b0a99fbf1d3784c9198
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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