Sulfuric Acid → 3-Bromo-5-nitrobenzonitrile

HRID 2070935Notes

Reaction equation

HRID 2070935 reaction equation
N[C:2]1[C:9]([Br:10])=[CH:8][C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]=1[C:4]#[N:5].OS(O)(=O)=O.N([O-])=O.[Na+].CCOC(C)=O>CCO.O>[Br:10][C:9]1[CH:2]=[C:3]([CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[CH:8]=1)[C:4]#[N:5]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 871732-Amino-3-bromo-5-nitrobenzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 51524253-Bromo-5-nitrobenzonitrileYield 82.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirring mixture of 1.2 g (4.96 mmol) of 2-amino-3-bromo-5-nitrobenzonitrile and 2.8 mL of H2SO4 in 28 mL of EtOH at 90° C. was added 2.5 g (36.2 mmol) of NaNO2 in several portions. After 13.5 h, EtOAc and H2O were added. The organic layer was washed with H2O and brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (5% EtOAc/hexanes) provided 927 mg of 3-bromo-5-nitrobenzonitrile in 82% yield as a yellow solid.

Workup

  1. washThe organic layer was washed with H2O and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash silica gel chromatography (5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8745fe3c8b5447aea8ef6342df5d67a3
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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