Water → 2-Methyl-5-phenylbenzonitrile

HRID 1883616Notes

Reaction equation

HRID 1883616 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[C:7]#[N:8].OB(O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(Cl)(Cl)Cl>[CH3:10][C:5]1[CH:4]=[CH:3][C:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][C:6]=1[C:7]#[N:8]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 129940045-Bromo-2-methylbenzonitrile

Product 1

HCID 111715372-Methyl-5-phenylbenzonitrileYield 71.4%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 27.4 g (140 mmol) of 5-bromo-2-methylbenzonitrile, 19.5 g (160 mmol) of dihydroxyphenylborane, 629 mg (2.8 mmol) of palladium acetate (II), 45.1 g (140 mmol) of tetrabutylammonium bromide, 48.4 g (350 mmol) of potassium carbonate and 280 ml of water was stirred at 75° C. for 11 hours under nitrogen flow. To the reaction solution was added chloroform, the organic layer was washed with water, dried over anhydrous magnesium sulfate, then, concentrated. The residue was re-crystallized from methanol to give 19.9 g (99.9 mmol) of 2-methyl-5-phenylbenzonitrile.

Workup

  1. washthe organic layer was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was re-crystallized from methanol

Sources & evidence

ORD record
ord-91d9e4e4b8564044855fb773b2b345fe
Source dataset
uspto-grants-2004_07
Patent number
US06762197B2

Reaction notes

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