(o-Chlorophenyl)acetonitrile → 2-Biphenylacetonitrile

HRID 1296998Notes

Reaction equation

HRID 1296998 reaction equation
[OH-].[OH-].[C:3]1([B+2])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F-].[K+].Cl[C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[CH2:15][C:16]#[N:17]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C1COCC1>[C:16]([CH2:15][C:14]1[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)#[N:17]

Participants

7

Reactant 3

HCID 76112(o-Chlorophenyl)acetonitrileHCID 522689Potassium FluorideHCID 178419127HCID 178419127, compound

Product 1

HCID 3341012-BiphenylacetonitrileYield 92.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 27342152-(Di-tert-butylphosphino)biphenylCatalystHCID 8028TetrahydrofuranSolvent

Procedure

An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol %), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol %), phenylboron dihydroxide (183 mg, 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) and 2-chlorobenzyl cyanide (152 mg, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with 1.0 M NaOH (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 178 mg (92%) of the title compound.

Workup

  1. customAn oven dried resealable Schlenk tube
  2. customwas evacuated
  3. customThe tube was evacuated
  4. additionwere added through a rubber septum
  5. customhad been completely consumed
  6. additionThe reaction mixture was then diluted with ether (30 mL)
  7. additionpoured into a separatory funnel
  8. washThe mixture was washed with 1.0 M NaOH (20 mL)
  9. extractionthe aqueous layer was extracted with ether (20 mL)
  10. washThe combined organic layers were washed with brine (20 mL)
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-9ca75c6ad2cd41fbb5e1b42ddbf78350
Source dataset
uspto-grants-2007_07
Patent number
US07247731B2

Reaction notes

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