hydroxylamine-O-sulfonic acid → 4-Bromo-2,5-difluorobenzonitrile

HRID 2179979Notes

Reaction equation

HRID 2179979 reaction equation
[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]=O)=[C:4]([F:11])[CH:3]=1.[NH2:12]OS(O)(=O)=O>O>[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([C:6]#[N:12])=[C:4]([F:11])[CH:3]=1

Participants

4

Reactant 2

HCID 76284hydroxylamine-O-sulfonic acidHCID 224890814-Bromo-2,5-difluorobenzaldehyde

Product 1

HCID 149849124-Bromo-2,5-difluorobenzonitrileYield 66.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Bromo-2,5-difluorobenzaldehyde (1.82 g, 8.3 mmol) and hydroxylamine-O-sulphonic acid (1.1 eq., 1.03 g) in water (40 ml) were heated to 100° C. for 6 h, cooled and extracted with ethyl acetate. The organic layer was dried (sodium sulphate) and evaporated to give the title compound as a pale yellow solid (1.2 g).

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried (sodium sulphate)
  4. customevaporated

Sources & evidence

ORD record
ord-af1af95b8a5e475cb281ccdf1f24c0d8
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

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