Sulfuric Acid → 1-Bromo-3-(difluoromethyl)-5-nitrobenzene

HRID 410539Notes

Reaction equation

HRID 410539 reaction equation
[F:1][CH:2]([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.OS(O)(=O)=O.C1C(=O)N([Br:25])C(=O)C1>O>[Br:25][C:7]1[CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=[C:3]([CH:2]([F:12])[F:1])[CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 67184N-bromobutanimideHCID 214079051-(Difluoromethyl)-3-nitrobenzene

Product 1

HCID 672481711-Bromo-3-(difluoromethyl)-5-nitrobenzeneYield 56.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(Difluoromethyl)-3-nitrobenzene (866 mg, 5.00 mmol) was added to cold conc. H2SO4 and then NBS (890 mg, 5.00 mmol) was added. The mixture was warmed to room temperature for 30 minutes then 50-60° C. for 1 h. The mixture was then poured in water and ice and extracted diethyl ether twice. The organic layer was washed with dilute aqueous NaHCO3 and brine. Purification by chromatography on silica gel (0-15% ethyl acetate in hexanes) yielded 1-bromo-3-(difluoromethyl)-5-nitrobenzene (710 mg, 2.82 mmol, 56.3%).

Workup

  1. extractionice and extracted diethyl ether twice
  2. washThe organic layer was washed with dilute aqueous NaHCO3 and brine
  3. customPurification by chromatography on silica gel (0-15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-01e7647611d94c9b943c280536db77a4
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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