反应详情

温度

-78 °C

4-Bromo-N-tert-butyl-3-methyl-benzenesulfonamide (10 g, 32.6 mmol) was dissolved in dry tetrahydrofurane, then cooled to −78° C. Triisopropyl borate (27.7 ml, 120.8 mmol, 3.7 equiv.) was added in one portion, followed by the dropwise addition of n-butyllithium solution 1.6M (75.5 ml, 120.8 mmol, 3.7 equiv.) at −78° C. The mixture was stirred overnight, then quenched dropwise with water. The organic solvent was evaporated and the pH adjusted to 3 with 0.5 M HCl. The residue was extracted with ethyl acetate and the combined organic extracts were washed with brine, dried over magnesiumsulfat-dihydrate, filtered and evaporated. The crude product was purified on silica-gel with ethyl acetate/n-heptane to give 2.82 g of the title product as yellow, waxy solid. MS (ES): m/e 270 (M−H)

1. customquenched dropwise with water
2. customThe organic solvent was evaporated
3. extractionThe residue was extracted with ethyl acetate
4. washthe combined organic extracts were washed with brine
5. dry with materialdried over magnesiumsulfat-dihydrate
6. filtrationfiltered
7. customevaporated
8. customThe crude product was purified on silica-gel with ethyl acetate/n-heptane