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

HRID 1892925Notes

Reaction equation

HRID 1892925 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-ea08b46a45cc46bea1fab3bb53468aa6
Source dataset
uspto-grants-2013_08
Patent number
US08507543B2

Reaction notes

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