反应详情

35.7 g (190 mmol) 2-(1,3,2-dioxaborinan-2-yl)benzonitrile, 31.9 g (158 mmol) 2-bromo-4-(tertbutyl)aniline, 3.6 g (3.16 mmol) tetrakis(triphenylphosphine) palladium(0) and 59.0 g (427 mmol) K2CO3 were heated to reflux in a 2 L flask containing 400 ml toluene and 300 mL ethanol. The reaction mixture was heated for 19 hours under constant N2 purge. HPLC of the reaction mixture indicated consumption of the starting aniline. The mixture was cooled and then filtered to remove the base. The base washed with EtOAc to remove trace organic. The combined filtrate was evaporated down to give impure oil. The oil was purified on a column of silica using 95/5/0.05 CH2Cl2/MeOH/NH4OH as eluent to obtain separation. The product fractions were evaporated of solvent and the resultant residue recrystallized from CH2Cl2/hexanes to yield 14.0 g of the target compound as white solids (35.5% yield, confirmed by GC-MS).

1. temperatureto reflux in a 2 L flask
2. temperatureThe reaction mixture was heated for 19 hours under constant N2
3. custompurge
4. customconsumption of the starting aniline
5. temperatureThe mixture was cooled
6. filtrationfiltered
7. customto remove the base
8. washThe base washed with EtOAc
9. customto remove trace organic
10. customThe combined filtrate was evaporated down
11. customto give impure oil
12. customThe oil was purified on a column of silica using 95/5/0.05 CH2Cl2/MeOH/NH4OH as eluent
13. customto obtain
14. customseparation
15. customThe product fractions were evaporated of solvent
16. customthe resultant residue recrystallized from CH2Cl2/hexanes