Potassium Cyanide → 2-(3,4-Bis(difluoromethoxy)phenyl)-2-hydroxyacetonitrile

HRID 1438172Notes

Reaction equation

HRID 1438172 reaction equation
[F:1][CH:2]([F:16])[O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([F:15])[F:14])[CH:7]=[O:8].[C-:17]#[N:18].[K+].OS([O-])=O.[Na+]>C(OCC)(=O)C.O>[F:1][CH:2]([F:16])[O:3][C:4]1[CH:5]=[C:6]([CH:7]([OH:8])[C:17]#[N:18])[CH:9]=[CH:10][C:11]=1[O:12][CH:13]([F:15])[F:14]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 145092693,4-Bis(difluoromethoxy)benzaldehydeHCID 23665763Sodium Bisulfite

Product 1

HCID 579426602-(3,4-Bis(difluoromethoxy)phenyl)-2-hydroxyacetonitrileYield 72.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 132A (470 mg, 2.0 mmol) in ethyl acetate (5 mL) was added a solution of KCN (676 mg) and NaHSO3 (1.08 g) dissolved in H2O (5 mL). It was left stirring overnight before it was extracted with ethyl acetate (2×50 mL). The combined organic extracts were dried and concentrated. The crude product was purified by silica gel chromatography to give 132B (383 mg, 72% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 5.56 (d, J=5.27 Hz, 1H) 6.32-6.77 (m, 2H) 7.32-7.36 (m, 1H) 7.40-7.44 (m, 1H) 7.45 (s, 1H).

Workup

  1. waitIt was left
  2. extractionwas extracted with ethyl acetate (2×50 mL)
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-25513f1243464c04ad147c83604b0c69
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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