反应详情

A 15-mL round-bottom flask was charged with 5-bromonaphthalene-2-sulfonic acid (2.346 g, 8.17 mmol) and DMF (8.17 mL) to give a green suspension. Thionyl chloride (1.193 mL, 16.34 mmol) was added dropwise, and the resulting orange mixture was stirred for 2 h. The mixture was poured into ice and extracted with DCM (three times). The combined organic extracts were washed with water, dried over sodium sulfate, filtered and concentrated. The residue was dissolved in DCM (35 mL), and the resulting solution was added to 2,3,4,5,6-pentafluorophenol (2.256 g, 12.26 mmol). Triethylamine (1.708 mL, 12.26 mmol) was added dropwise, and the resulting mixture was stirred for 30 min and then concentrated. The residue was taken up in DCM and filtered. The filtrate was concentrated, and the product was purified by chromatography on silica gel (0 to 20% EtOAc/Heptane) to afford perfluorophenyl 5-bromonaphthalene-2-sulfonate (2.4426 g, 5.39 mmol) as a light-yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm=8.64-8.46 (m, 2H), 8.13-7.95 (m, 3H), 7.63-7.47 (m, 1H).

1. customto give a green suspension
2. additionThe mixture was poured into ice
3. extractionextracted with DCM (three times)
4. washThe combined organic extracts were washed with water
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. dissolutionThe residue was dissolved in DCM (35 mL)
9. stirringthe resulting mixture was stirred for 30 min
10. concentrationconcentrated
11. filtrationfiltered
12. concentrationThe filtrate was concentrated
13. customthe product was purified by chromatography on silica gel (0 to 20% EtOAc/Heptane)