Acetonitrile → 4-Cyclopropylcarbonylphenylacetonitrile

HRID 1018075Notes

Reaction equation

HRID 1018075 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH:11]2[CH2:13][CH2:12]2)=[O:10])=[CH:5][CH:4]=1.[C-]#N.[K+].[C:17](#[N:19])C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH:11]1([C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][C:17]#[N:19])=[CH:4][CH:5]=2)=[O:10])[CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 9032Potassium CyanideHCID 15512829(4-(Bromomethyl)phenyl)(cyclopropyl)methanone

Product 1

HCID 155128314-Cyclopropylcarbonylphenylacetonitrile

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×

Procedure

Mix (4-bromomethyl-phenyl)-cyclopropyl-methanone (5.0 g, 21 mmol), potassium cyanide (2.0 g, 30 mmol), tetra-butylammonium bromide (150 mg), water (5 mL) and acetonitrile (50 mL). Mechanically stir at room temperature for 3 hours, pour into water (450 mL) and stir overnight. Collect by filtration and recrystallize (hexane) to give the title compound as a white crystalline solid; mp 86-87° C.

Workup

  1. stirringstir overnight
  2. filtrationCollect by filtration
  3. customrecrystallize (hexane)

Sources & evidence

ORD record
ord-b7988ee3721149e3be397d4359f4fd43
Source dataset
uspto-grants-2002_11
Patent number
US06479663B2

Reaction notes

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