hydroxylamine-O-sulfonic acid → 2,4-Difluoro-6-methoxybenzonitrile

HRID 1808583Notes

Reaction equation

HRID 1808583 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([O:11][CH3:12])[C:3]=1[CH:4]=O.[NH2:13]OS(O)(=O)=O>O>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([O:11][CH3:12])[C:3]=1[C:4]#[N:13]

Participants

4

Reactant 2

HCID 76284hydroxylamine-O-sulfonic acidHCID 588540582,4-Difluoro-6-methoxybenzaldehyde

Product 1

HCID 580544482,4-Difluoro-6-methoxybenzonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

2,4-Difluoro-6-methoxybenzaldehyde (for a preparation see Intermediate 47) (34.5 g, 0.20 mol) and hydroxylamine-o-sulfonic acid (24.95 g, 0.22 mol) were charged to a round-bottom flask. Water (500 mL) was added and the suspension was heated at 110° C. for 3 h. After TLC shows reaction to be complete, it was cooled in ice-water and extracted thrice with ethyl acetate. The organic solutions were dried (MgSO4) and evaporated, and the residue was purified by dry flash chromatography (DCM eluent) to give the title compound (32.05 g, 95%) as a pale pink solid.

Workup

  1. additionwere charged to a round-bottom flask
  2. customreaction
  3. extractionextracted thrice with ethyl acetate
  4. dry with materialThe organic solutions were dried (MgSO4)
  5. customevaporated
  6. customthe residue was purified
  7. dry with materialby dry flash chromatography (DCM eluent)

Sources & evidence

ORD record
ord-e1aea9e93ef4430095560a7fe9eed48f
Source dataset
uspto-grants-2013_01
Patent number
US08357716B2

Reaction notes

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