Nitric Acid → 3-Bromo-4-methoxy-5-nitrobenzonitrile

HRID 2093612Notes

Reaction equation

HRID 2093612 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[C:5]#[N:6].[N+:12]([O-])([OH:14])=[O:13]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[C:9]=1[O:10][CH3:11])[C:5]#[N:6]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 7360493-Bromo-4-methoxybenzonitrile

Product 1

HCID 671405393-Bromo-4-methoxy-5-nitrobenzonitrile

Procedure

3-bromo-4-methoxybenzonitrile (5.22 g, 24.62 mmol) was added to rapidly stirring fuming nitric acid (10 ml, 201 mmol) at 0° C. The ice bath was removed and the reaction mixture was stirred for 2 h at room temperature. The reaction mixture was diluted with ethyl acetate and water, and then the organic layer was washed with water and brine, dried (sodium sulfate), filtered, and concentrated in vacuo to afford the title compound, which was carried on without further purification.

Workup

  1. customThe ice bath was removed
  2. additionThe reaction mixture was diluted with ethyl acetate and water
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a3516b0d3554541bfcf46e1c675d6f0
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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