Water → 1-Bromo-5-fluoro-2-methyl-3-nitrobenzene

HRID 1365851Notes

Reaction equation

HRID 1365851 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.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

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 67184N-bromobutanimideHCID 679654-Fluoro-2-nitrotoluene

Product 1

HCID 27733851-Bromo-5-fluoro-2-methyl-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 4-fluoro-2-nitrotoluene (10.0 g, 64.4 mmol) in trifluoroacetic acid (40 mL) was added concentrated sulfuric acid (12.5 mL) followed by N-bromosuccinimide (17.2 g, 96.6 mmol) and the reaction mixture was stirred at RT for 16 h. The reaction mixture was then poured onto ice and water and stirred for 15 min. The product was then extracted into EtOAc and the organic layer washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound as a pale oil which crystallised out on standing (11.76 g, 77%). NMR δH (300 MHz, CDCl3) 2.59 (s, 3H), 7.50 (dd, J=2.8, 7.6, 1H) and 7.58 (dd, J=2.9, 7.4, 1H).

Workup

  1. stirringstirred for 15 min
  2. extractionThe product was then extracted into EtOAc
  3. washthe organic layer washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d5a6359c41c427a97f3a0aabca11684
Source dataset
uspto-grants-2011_02
Patent number
US07893060B2

Reaction notes

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