Potassium Cyanide → (3-Fluoro-5-methoxyphenyl)acetonitrile

HRID 2368917Notes

Reaction equation

HRID 2368917 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([F:11])[CH:4]=1.[C-:12]#[N:13].[K+]>CS(C)=O.O>[F:11][C:5]1[CH:4]=[C:3]([CH2:2][C:12]#[N:13])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 72211834HCID 72211834, compound

Product 1

HCID 26985457(3-Fluoro-5-methoxyphenyl)acetonitrileYield 93.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
45 °C

Procedure

To a solution of 1-(chloromethyl)-3-fluoro-5-methoxybenzene (2.9 g, 17 mmol) in DMSO (20 mL), a solution of KCN (2.2 g, 34 mmol) and KI (5.6 g, 34 mmol) in H2O (10 mL) was added. The mixture was stirred at 45° C. for 6 h, poured into H2O (20 mL), and extracted with DCM (3×30 mL). The organic phase was washed with brine (2×10 mL), dried over Na2SO4, and concentrated to give 2.62 g of 2-(3-fluoro-5-methoxyphenyl)acetonitrile. 1H NMR (CDCl3): δ 6.62-6.68 (m, 2H), 6.56-6.60 (m, 1H), 3.80 (s, 3H), 3.70 (s, 2H).

Workup

  1. extractionextracted with DCM (3×30 mL)
  2. washThe organic phase was washed with brine (2×10 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ee94747b36f54591a37cec1b1df6f80d
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

Loading…