Diethanolamine → 2-Cyano-4'-methylbiphenyl

HRID 1292572Notes

Reaction equation

HRID 1292572 reaction equation
Cl[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:10]1([CH3:19])[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+].N(CCO)CCO.C1C=C(S([O-])(=O)=O)C=C(P(C2C=CC=C(S([O-])(=O)=O)C=2)C2C=CC=C(S([O-])(=O)=O)C=2)C=1.[Na+].[Na+].[Na+].O>CS(C)=O.[Pd](Cl)Cl.C([O-])(=O)C.[Na+].O.CC1C=CC(C)=CC=1>[C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[C:13]1[CH:14]=[CH:15][C:10]([CH3:19])=[CH:11][CH:12]=1)#[N:5]

Participants

11

Reactant 5

HCID 8113DiethanolamineHCID 10340Sodium CarbonateHCID 133912-ChlorobenzonitrileHCID 79799Tolylboronic acidHCID 53487040Sodium 3,3',3''-phosphinetriyltribenzenesulfonate hydrate

Product 1

HCID 1455122-Cyano-4'-methylbiphenylYield 83.2%

Reagents, catalysts & solvents 5

HCID 24290Palladium ChlorideCatalystHCID 517045Sodium AcetateCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 7809P-XyleneSolvent

Procedure

15 g of 2-chlorobenzonitrile, 14.8 g of p-tolueneboronic acid and 28.9 g of sodium carbonate were heated to 120° C. with 50 ml of p-xylene, 40 ml of diethanolamine and 10 ml of water. At 80° C., a mixture of 19.3 mg of palladium chloride, 17.9 mg of sodium acetate and 0.55 ml of TPPTS/ H2O solution (0.6 molar) in 2.5 ml of DMSO was added. After the reaction was complete, the phases were separated. The aqueous phase was washed with 50 ml of toluene. The combined organic phases were washed with 20 ml of water and subsequently dried over sodium sulfate. Crystallization from n-heptane gave 17.5 g of 2-cyano-4'-methylbiphenyl.

Workup

  1. additionwas added
  2. customthe phases were separated
  3. washThe aqueous phase was washed with 50 ml of toluene
  4. washThe combined organic phases were washed with 20 ml of water
  5. dry with materialsubsequently dried over sodium sulfate
  6. customCrystallization from n-heptane

Sources & evidence

ORD record
ord-4a1737518f094e3b9c8df1b577d8f91e
Source dataset
uspto-grants-1998_05
Patent number
US05756804

Reaction notes

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