反应详情

3-(1-adamantyl)-4-methoxyphenylboronic acid (150 mg, 0.32 mmol), 6-bromo-2-naphtalenyl trifluoromethanesulphonate (93 mg, 0.26 mmol), K3PO4 (222 mg, 1.05 mmol), KBr (34 mg, 0.29 mmol) and THF (2 ml) were introduced into a Schlenk tube. Next, the reaction mixture was deoxygenated (3 froze/thaw cycles). Next, Pd(PPh3)4 (15 mg, 0.013 mmol) was added and the mixture was again deoxygenated (2 froze/thaw cycles). After heating at reflux for 18 h, the mixture was brought at room temperature and was diluted with CHCl3 (5 ml). The solution was filtered through celite and washings with CHCl3 (2×5 ml) were carried out. The evaporation of the joined organic phases gave a residue which was redissolved in CHCl3 (5 ml) and washed with H2O (2×5 ml). The organic phase was dried with Na2SO4 and after evaporation to dryness, a crude was obtained (97 mg) which was recrystallized with the minimum volume of toluene at reflux. The title compound was obtained (68 mg, 58%) as a pale yellow powder. IR (KBr) 2900, 2847, 1600, 1489, 1456, 1442, 1262, 1237, 1178, 1142, 1103, 1061, 1026, 877, 809 y 470. M/Z (El) 448 [M+ (81Br), 76%] y 446 [M+ (79Br), 100].

1. customNext, the reaction mixture was deoxygenated (3 froze/thaw cycles)
2. customthe mixture was again deoxygenated (2 froze/thaw cycles)
3. temperatureAfter heating
4. temperatureat reflux for 18 h
5. customwas brought at room temperature
6. additionwas diluted with CHCl3 (5 ml)
7. filtrationThe solution was filtered through celite and washings with CHCl3 (2×5 ml)
8. customThe evaporation of the joined organic phases
9. customgave a residue which
10. washwashed with H2O (2×5 ml)
11. dry with materialThe organic phase was dried with Na2SO4
12. customafter evaporation to dryness
13. customa crude was obtained (97 mg) which
14. customwas recrystallized with the minimum volume of toluene
15. temperatureat reflux