2-Bromobenzyl cyanide → 2-(2-Cyclopropylphenyl)acetonitrile

HRID 254514

Reaction equation

HRID 254514 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].[CH:11]1(B(O)O)[CH2:13][CH2:12]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH:11]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][C:9]#[N:10])[CH2:13][CH2:12]1

Participants

8

Reactant 4

HCID 296252-Bromobenzyl cyanideHCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acid

Product 1

HCID 589517752-(2-Cyclopropylphenyl)acetonitrileYield 63.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.784 g (4 mmol) 2-bromophenyl-acetonitrile in 16 ml toluene were added 0.8 ml water, 0.412 g (4.8 mmol) cyclopropylboronic acid, 2.97 g (14 mmol) tribasic potassium phosphate, 0.1 12 g (0.4 mmol) tricyclohexylphosphine and 0.045 g (0.2 mmol) palladium(II) acetate. The reaction mixture was stirred at 100° C. for 2 days. The solvent was evaporated and the residue taken up in water and ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered and evaporated. The residue was purified using column chromatography (SiO2, heptane/ethyl acetate 98:2) to yield 0.40 g of (2-cyclopropyl-phenyl)-acetonitrile as a light-yellow oil that was used directly for the next step.

Workup

  1. customThe solvent was evaporated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-4d171b5178dd4365b39a40fdf193045c
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Linked notes

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