Sodium Cyanide → HCID 15364226, compound

HRID 1397352Notes

Reaction equation

HRID 1397352 reaction equation
[C-:1]#[N:2].[Na+].[C:4]1([C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[CH2:13]Br)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CN(C=O)C>[C:10]1([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:17]=[CH:16][CH:15]=[C:12]([CH2:13][C:1]#[N:2])[CH:11]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 38644053-(Bromomethyl)biphenyl

Product 1

HCID 15364226HCID 15364226, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaCN (1.1 g, 22.26 mmol) was added to a solution of 3-phenylbenzyl bromide (5.0 g, 20.23 mmol) in dry DMF (100 mL). The resulting reaction mixture was stirred at room temperature for 3 h and then quenched with water. The organic product was extracted with EtOAc and the combined extracts were washed with H2O and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 5% EtOAc in petroleum ether) to afford 2-([1,1′-biphenyl]-3-yl)acetonitrile (3.8 g, yield 97%). 1H NMR (300 MHz, CDCl3) δ 7.61-7.56 (m, 4H), 7.50-7.45 (m, 3H), 7.42-7.36 (m, 1H), 7.34-7.31 (m, 1H), 3.83 (s, 2H).

Workup

  1. customThe resulting reaction mixture
  2. customquenched with water
  3. extractionThe organic product was extracted with EtOAc
  4. washthe combined extracts were washed with H2O and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 5% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-7badcd1d43c4416ba1218ce8ae63d8d5
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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