Sulfuric Acid → 1-Bromo-5-fluoro-2-methyl-3-nitrobenzene

HRID 2262016Notes

Reaction equation

HRID 2262016 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.S(=O)(=O)(O)O.[Br:17]N1C(=O)CCC1=O>FC(F)(F)C(O)=O>[Br:17][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]=1[CH3:8]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 67184N-bromobutanimideHCID 679654-Fluoro-2-nitrotoluene

Product 1

HCID 27733851-Bromo-5-fluoro-2-methyl-3-nitrobenzeneYield 114.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 4-fluoro-2-nitrotoluene (3.44 g) in trifluoroacetic acid (13 mL) was added concentrated sulfuric acid (4 mL) followed by N-bromosuccinimide (5.92 g). The reaction mixture was stirred for 16 h and was then quenched with brine, extracted into ethyl acetate, and dried (MgSO4). The solvent was removed in vacuo to furnish crude 1-bromo-5-fluoro-2-methyl-3-nitro-benzene (5.96 g).

Workup

  1. customwas then quenched with brine
  2. extractionextracted into ethyl acetate
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-24d70ea3d04443e0bdb2f7caa666bfeb
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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