反应详情

温度

-78 °C

In a flame-dried flask under nitrogen, 0.53 mL (3.79 mmol) of diisopropylamine were dissolved in 5 mL of tetrahydrofuran (THF) and the solution cooled to −78° C. n-Butyllithium (3.75 mmol as a 2.5 M solution in hexanes) was added and the resulting mixture brought to 0° C. with continued stirring for 10 min. The reaction mixture was again cooled to −78° C. and to this mixture added a solution of 1.0 g (3.40 mmol) of the product from Method C in 10 mL of THF over a 10 min period. The reaction mixture was stirred for 1 h at −78° C., at which time, 8.2 mL (4.10 mmol) of a 0.5 M solution of zinc chloride in THF was added, the reaction mixture was brought to room temperature and stirred for 1 h. Iodobenzene (0.46 mL/4.11 mmol) and a suspension of 197 mg of tetrakis(triphenylphosphine) palladium in 2 mL of THF were added. The resulting mixture was stirred at reflux for 3 h., cooled to room temperature, and partitioned between dichloromethane and water. The aqueous layer was acidified with 1 N HCl and extracted twice with dichloromethane. The dichloromethane layers were combined; washed with 1 N HCl and brine, dried over magnesium sulfate (MgSO4), filtered and concentrated in vacuo to obtain the title compound. LRMS: 370, 372 (M+2).

1. additionwas added
2. custombrought to 0° C.
3. additionwas added
4. customwas brought to room temperature
5. stirringstirred for 1 h
6. additionwere added
7. stirringThe resulting mixture was stirred
8. temperatureat reflux for 3 h.
9. temperaturecooled to room temperature
10. custompartitioned between dichloromethane and water
11. extractionextracted twice with dichloromethane
12. washwashed with 1 N HCl and brine
13. dry with materialdried over magnesium sulfate (MgSO4)
14. filtrationfiltered
15. concentrationconcentrated in vacuo