Potassium Cyanide → (5-Tert-butyl-2-methoxyphenyl)acetonitrile

HRID 406354Notes

Reaction equation

HRID 406354 reaction equation
[C-:1]#[N:2].[K+].Br[CH2:5][C:6]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:9]=[CH:8][C:7]=1[O:16][CH3:17].COC(C)(C)C>CS(C)=O>[C:12]([C:10]1[CH:9]=[CH:8][C:7]([O:16][CH3:17])=[C:6]([CH2:5][C:1]#[N:2])[CH:11]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 15413tert-Butyl methyl etherHCID 666189372-Bromomethyl-4-tert-butyl-1-methoxybenzene

Product 1

HCID 66618992(5-Tert-butyl-2-methoxyphenyl)acetonitrileYield 30.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium cyanide (2.96 g) was added to a solution of 2-bromomethyl-4-tert-butyl-1-methoxybenzene (7.78 g) in dimethyl sulfoxide (50 mL), and the mixture was stirred at room temperature for 16 hours. Ice and tert-butyl methyl ether were added to the reaction solution, and the organic layer was separated. The aqueous layer was reextracted with tert-butyl methyl ether. The combined organic layers were sequentially washed with water (twice) and brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: heptane→ethyl acetate:heptane=1:49). The target fraction was concentrated. The resulting residue was triturated with hexane to obtain 1.90 g of the title compound. The trituration mother liquor was concentrated. Then, the resulting residue was triturated with hexane to obtain 0.47 g of the title compound. The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. washThe combined organic layers were sequentially washed with water (twice) and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: heptane→ethyl acetate:heptane=1:49)
  6. concentrationThe target fraction was concentrated
  7. customThe resulting residue was triturated with hexane

Sources & evidence

ORD record
ord-19eb5cbdb6a144e999f26434d232a1b2
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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