Nitric Acid → HCID 68584619, compound

HRID 17530Notes

Reaction equation

HRID 17530 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[C:5]#[N:6].[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:7]([N+:11]([O-:13])=[O:12])=[C:4]([CH:3]=1)[C:5]#[N:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1235793-Bromo-4-fluorobenzonitrile

Product 1

HCID 68584619HCID 68584619, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

3-Bromo-4-fluorobenzonitrile (25 g, 0.125 mol) was dissolved in concentrated sulfuric acid (200 ml), and at 0° C., fuming nitric acid was dropwise added at 0° C., taking 1 hour. After stirred for 30 minutes at the same temperature, this was heated up to room temperature, taking 1.5 hours. This was gradually poured into ice. The formed precipitate was collected by filtration with washing with water, and dried under reduced pressure. The collected yellow powder was fractionated with chloroform and aqueous 1 M sodium hydroxide solution. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was well dried under reduced pressure to obtain the entitled compound (14.7 g, 48%) as a yellow powder.

Workup

  1. customat 0° C.
  2. additionwas dropwise added at 0° C.
  3. waittaking 1.5 hours
  4. additionThis was gradually poured into ice
  5. filtrationThe formed precipitate was collected by filtration
  6. washwith washing with water
  7. customdried under reduced pressure
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was evaporated away
  11. customthe resulting residue was well dried under reduced pressure

Sources & evidence

ORD record
ord-3e240567bde4449c8214003cc724eb2f
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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