反应详情

温度

80 °C

Difluorozinc (6.093 g, 58.92 mmol) was added to a round bottomed flask, which was flushed with nitrogen. Pd(tBu3P)2 (2 g, 3.835 mmol) was then added under nitrogen stream. 2-Bromo-4-tert-butyl-5-nitro-phenol (16.15 g, 58.92 mmol) dissolved in DMF (80.75 mL) was then added to the flask. The reaction mixture was an orange suspension. (1-Methoxy-2-methyl-prop-1-enoxy)trimethylsilane (21.61 g, 25.13 mL, 117.8 mmol) was added to the mixture and the resulting mixture was heated to 80° C. and stirred for 16 h. When complete, the reaction mixture was cooled to ambient temperature and filtered through Celite®. The filter cake was washed with MTBE (536.0 mL) and water (893.3 mL) was added to the filtrate. The mixture was stirred for 15 min and settled for another 15 min. The layers were separated and 0.5M HCl (500 mL, 250.0 mmol) was added to the organic phase. The layers were separated and the organic layer was washed with water (500 mL). The layers were separated and the organic layer was washed with NaCl (500 mL; 8 wt %). The organic layer was separated and the solvent removed in vacuo. The crude product was obtained as a brown crystalline solid and was then purified through a silica plug, using hexane:MTBE 20:1-10:1 as an eluent. The fractions containing product were combined and the solvent removed in vacuo to give the pure product as a white crystalline solid. 1H-NMR (400 MHZ, DMSO-d6) δ 7.80 (s, 1H); 7.62 (s, 1H); 1.49 (s, 6H); 1.34 (s, 9H)

1. customwhich was flushed with nitrogen
2. additionwas then added to the flask
3. temperatureWhen complete, the reaction mixture was cooled to ambient temperature
4. filtrationfiltered through Celite®
5. washThe filter cake was washed with MTBE (536.0 mL) and water (893.3 mL)
6. additionwas added to the filtrate
7. stirringThe mixture was stirred for 15 min
8. waitsettled for another 15 min
9. customThe layers were separated
10. customThe layers were separated
11. washthe organic layer was washed with water (500 mL)
12. customThe layers were separated
13. washthe organic layer was washed with NaCl (500 mL; 8 wt %)
14. customThe organic layer was separated
15. customthe solvent removed in vacuo
16. customThe crude product was obtained as a brown crystalline solid
17. customwas then purified through a silica plug
18. additionThe fractions containing product
19. customthe solvent removed in vacuo