反应详情

温度

80 °C

Following the procedure described in J. Org. Chem. 1997, 62, 6507, combine N-(2-bromo-5-trifluoromethylphenyl)carbamic acid ethyl ester (34.33 g, 110 mmol), triethylamine (300 mL), dichlorobis (triphenylphosphine)palladium(II) (5.4 g, 7.7 mmol), and copper (I) iodide (1.47 g, 7.7 mmol). Evacuate the dark solution and fill with N2 twice and then quickly add (trimethylsilyl)acetylene (16.21 g, 165 mmol, 23.32 mL) with vigorous stirring. Heat to 80° C. When TLC indicates absence of the starting material, add water and Et2O and filter through celite and evaporate the filtrate in vacuo to give a residue. Dilute residue with water and extract with Et2O, combine the organic layers and remove the evaporate to give a dark brown oil. Absorb the oil onto silica gel and load onto a short column of silica gel equilibrated with 100% hexanes. Wash with 100% hexanes (2 L) and elute the product with 1% EtOAc in hexanes. Pool fractions containing the product and remove in vacuo the solvent to give 5-trifluoromethyl-2-trimethylsilanylethynyl phenylamine as a red/brown oil; MS (IS): m/z 330 (M+H)+.

1. customEvacuate the dark solution and fill with N2 twice
2. filtrationfilter through celite
3. customevaporate the filtrate in vacuo
4. customto give a residue
5. extractionDilute residue with water and extract with Et2O
6. customremove the
7. customevaporate
8. customto give a dark brown oil
9. customAbsorb the oil onto silica gel and load onto a short column of silica gel
10. washWash with 100% hexanes (2 L)
11. washelute the product with 1% EtOAc in hexanes
12. additionPool fractions containing the product
13. customremove in vacuo the solvent