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

HRID 2365200Notes

Reaction equation

HRID 2365200 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.C(OCC)(=O)C>[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

6

Reactant 3

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

Product 1

HCID 27733851-Bromo-5-fluoro-2-methyl-3-nitrobenzeneYield 82.2%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-fluoro-2-nitrotoluene (2.0 g) in trifluoroacetic acid (8 ml) was added concentrated sulfuric acid (2.5 ml) followed by N-bromosuccinimide (3.4 g). After stirring for 24 hours the reaction mixture was then diluted with ethyl acetate, washed with water, brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified by flash chromatography to give 1-bromo-5-fluoro-2-methyl-3-nitro-benzene (2.48 g).

Workup

  1. washwashed with water, brine
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4d313bc5e17e466fbd1547284a5f629b
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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