Water → 2-[4-(4-Chloro-butyryl)-phenyl]-2-methyl-propionitrile

HRID 413519Notes

Reaction equation

HRID 413519 reaction equation
Br[C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:16])[CH2:12][CH2:13][CH2:14][Cl:15])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].C[Si]([C:21]#[N:22])(C)C.[Sn](Cl)(Cl)(Cl)Cl.O>C(Cl)Cl>[Cl:15][CH2:14][CH2:13][CH2:12][C:11]([C:8]1[CH:7]=[CH:6][C:5]([C:2]([CH3:4])([CH3:3])[C:21]#[N:22])=[CH:10][CH:9]=1)=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 24287Tin tetrachlorideHCID 82115Trimethylsilyl cyanideHCID 100635791-Butanone, 1-[4-(1-bromo-1-methylethyl)phenyl]-4-chloro-

Product 1

HCID 155128302-[4-(4-Chloro-butyryl)-phenyl]-2-methyl-propionitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 1-[4-(1-bromo-1-methyl-ethyl)-phenyl]-4-chloro-butan-1-one (2.00 g, 6.59 mmol) in anhydrous methylene chloride (20 mL) and place under an argon atmosphere. Add trimethylsilyl cyanide (1.10 mL, 8.25 mmol) followed by tin (IV) chloride (0.20 mL, 1.7 mmol) via syringe. Stir at reflux for 1 hour, add water (20 mL) and stir for an additional ½ hour. Separate the layers and extract the aqueous layer with methylene chloride. Combine the organic layers, wash with brine, dry (MgSO4), filter and evaporate the solvent in vacuo. Purify by silica gel chromatography (15% ethyl acetate/hexane) to give the title compound as a white solid; mp 79-80° C.

Workup

  1. temperatureat reflux for 1 hour
  2. stirringstir for an additional ½ hour
  3. customSeparate the layers
  4. extractionextract the aqueous layer with methylene chloride
  5. washwash with brine
  6. dry with materialdry (MgSO4)
  7. filtrationfilter
  8. customevaporate the solvent in vacuo
  9. customPurify by silica gel chromatography (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-40a0d57aed3147baa8434d32b8677ce7
Source dataset
uspto-grants-2003_05
Patent number
US06566526B2

Reaction notes

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