Potassium Cyanide → [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]acetonitrile

HRID 1183277Notes

Reaction equation

HRID 1183277 reaction equation
Br[CH2:2][C:3]1[C:4]([CH3:15])=[N:5][O:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1.[C-:16]#[N:17].[K+]>CN(C=O)C>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]2[O:6][N:5]=[C:4]([CH3:15])[C:3]=2[CH2:2][C:16]#[N:17])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 665772234-Bromomethyl-5-(4-bromo-phenyl)-3-methyl-isoxazole

Product 1

HCID 66577425[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]acetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To 4-bromomethyl-5-(4-bromo-phenyl)-3-methyl-isoxazole (10.74 mmol) in DMF (30 mL) was added potassium cyanide (0.729 g, 10.74 mmol), and the reaction was stirred at 65° C. overnight. After aqueous workup, the crude material was purified by silica gel chromatography (0-70% EtOAc in hexanes) to give the title compound.

Workup

  1. customAfter aqueous workup, the crude material was purified by silica gel chromatography (0-70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ef12515f12994659a3a659ffea52c7e6
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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