Hydrochloric Acid → 2-Chloro-2-(4-phenoxyphenyl)propionitrile

HRID 1016538Notes

Reaction equation

HRID 1016538 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15](C2C=CC=CC=2)=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([C:27]#[N:28])(C)C.[ClH:29]>C(Cl)Cl.[I-].[Mg+2].[I-]>[Cl:29][C:14]([C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:13][CH:12]=1)([CH3:15])[C:27]#[N:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 82115Trimethylsilyl cyanideHCID 28240562-(4-Phenoxyphenyl)-1-phenyl-1-ethanone

Product 1

HCID 120563902-Chloro-2-(4-phenoxyphenyl)propionitrile

Reagents, catalysts & solvents 2

HCID 5462737Magnesium diiodideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-phenoxyphenylacetophenone (6.36 g), trimethylsilylcyanide (3.96 g) and magnesium iodide (10 mg) in methylene chloride (30 ml) was stirred for 12 hrs at room temperature, 156 hydrochloric acid (10 ml) was then added. The mixture was again stirred for 8 hrs at room temperature. The organic layer was separated and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was dissolved in benzene (50 ml) and pyridine (2.37 g) and thionyl chloride (4.76 g) were added at 0° C. with stirring. The reaction mixture was stirred for an additional 3 hrs at room temperature and then the solvent was evaporated. The residue was purified by column chromatography to give 7.09 g of 2-chloro-2-(4-phenoxyphenyl)propionitrile as an oil.

Workup

  1. stirringThe mixture was again stirred for 8 hrs at room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in benzene (50 ml)
  6. additionpyridine (2.37 g) and thionyl chloride (4.76 g) were added at 0° C.
  7. stirringwith stirring
  8. stirringThe reaction mixture was stirred for an additional 3 hrs at room temperature
  9. customthe solvent was evaporated
  10. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-767406a608fd48ce9617e3ef0ada1853
Source dataset
uspto-grants-2002_11
Patent number
US06476055B1

Reaction notes

Loading…