반응 #456832

ord-273d7e61afd3408f82c30d9f7e75dba0

반응 방정식

N#Cc1ccccc1Cl
2-chlorobenzonitrile
Cc1ccc(B(O)O)cc1
p-tolueneboronic acid
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
O.O=S(=O)([O-])c1cccc(P(c2cccc(S(=O)(=O)[O-])c2)c2cccc(S(=O)(=O)[O-])c2)c1.[Na+].[Na+].[Na+]
TPPTS H2O
Cc1ccc(-c2ccccc2C#N)cc1
2-cyano-4'-methylbiphenyl
수율 84.6%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타the phases were separated
  2. 2
    세척The aqueous phase was washed with 50 ml of toluene
  3. 3
    세척The combined organic phases were washed with 20 ml of water
  4. 4
    건조subsequently dried over sodium sulfate
  5. 5
    기타Crystallization from n-heptane

실험 절차

15 g of 2-chlorobenzonitrile, 14.8 g of p-tolueneboronic acid and 28.9 g of sodium carbonate in 50 ml of p-xylene, 40 ml of triethanolamine and 10 ml of water were heated to 120° C. At 80° C., 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 were 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 17.8 g of 2-cyano-4'-methylbiphenyl.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US06140265uspto-grants-2000_10