Potassium Cyanide → 4-Chloro-3-cyanomethyl-5-methyl-benzonitrile

HRID 2194791Notes

Reaction equation

HRID 2194791 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH3:12])[C:10]=1[Cl:11])[C:6]#[N:7].[C-:13]#[N:14].[K+]>C(O)C.O.C(OCC)(=O)C>[Cl:11][C:10]1[C:9]([CH3:12])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:2][C:13]#[N:14]

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 670504963-Bromomethyl-4-chloro-5-methyl-benzonitrile

Product 1

HCID 670504934-Chloro-3-cyanomethyl-5-methyl-benzonitrileYield 48%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Bromomethyl-4-chloro-5-methyl-benzonitrile (0.9938 g, 4.06 mmol), potassium cyanide (0.529 g, 8.12 mmol) in ethanol (5.0 mL) and H2O (2.5 mL) was heated at 85° C. for 3 hr. The reaction mixture was cooled, diluted with ethyl acetate, washed with brine, dried (MgSO4), concentrated and purified by flash column chromatography (silica gel, 0 to 30% ethyl acetate/hexane) to give 4-chloro-3-cyanomethyl-5-methyl-benzonitrile as a white solid (0.3707 g, 48%). 1H NMR (300 MHz, CDCl3): 7.61 (s, 1H), 7.51 (s, 1H), 3.83 (s, 2H), 2.40 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by flash column chromatography (silica gel, 0 to 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-122627f21d7c456b9c24e131dddc5d7e
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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