反应详情

温度

80 °C

To a solution of 2-bromo-6-fluoro-4-nitro-phenylamine (11 g, 47 mmol) in dry Et3N (100 mL) was added CuI (445 mg, 5% mol), Pd(PPh3)2Cl2 (550 mg, 5% mol) and 3,3-dimethyl-but-1-yne (9.6 g, 120 mmol) under N2 protection. The mixture was stirred at 80° C. for 10 h. The reaction mixture was filtered, poured into ice (100 g), and extracted with EtOAc (50 mL×3). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 50:1) to give 2-(3,3-dimethyl-but-1-ynyl)-6-fluoro-4-nitro-phenylamine (4.0 g, 36%). 1H NMR (400 MHz, CDCl3) δ 8.02 (d, J=1.2 Hz, 1H), 7.84 (dd, =2.4, 10.8 Hz, 1H), 4.85 (brs, 2H), 1.36 (s, 9H).

1. filtrationThe reaction mixture was filtered
2. additionpoured into ice (100 g)
3. extractionextracted with EtOAc (50 mL×3)
4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
5. customevaporated under vacuum
6. customto give the crude product, which
7. customwas purified by column chromatography on silica gel (petroleum ether/ethyl acetate 50:1)