Acetonitrile → 2-Biphenylacetonitrile

HRID 1374841Notes

Reaction equation

HRID 1374841 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C-]#N.[K+].C1OCCOCCOCCOCCOCCOC1.[C:36](#[N:38])C>O>[C:4]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][C:36]#[N:38]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 2633651-(Bromomethyl)-2-phenylbenzene

Product 1

HCID 3341012-Biphenylacetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(Bromomethyl)biphenyl (1.35 g, 5.48 mmol), potassium cyanide (368 mg, 5.65 mmol), and a catalytic amount of 18-crown-6 ether were added to acetonitrile (10 ml), and the mixture was heated under reflux for 5 days. The reaction mixture was added with water and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium bicarbonate solution and saturated brine, and dried over magnesium sulfate. Insoluble solids were removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting oil was purified by silica gel column chromatography (ethyl acetate-hexane) to obtain the title compound as colorless solid (1.07 g, yield: quantitative).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 days
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium bicarbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customInsoluble solids were removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting oil was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-4fb1bbc0107848d58f5e71a0d33626a6
Source dataset
uspto-grants-2007_01
Patent number
US07166617B2

Reaction notes

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