反应详情

温度

80 °C

1-Bromo-3-tert-butoxy-5-fluorobenzene (56.1 g), benzophenone (50.9 g), NaOMe (50.5 g) and 2,2′-Bis-diphenylphosphanyl-[1,1′]binaphthalenyl (17.5 g) are dissolved in toluene (500 ml). The reaction mixture is flushed with argon, Pd2(dba)3 (5.4 g) is added and the reaction mixture is heated to 80° C. for 40 hours. The reaction mixture is quenched with water. The organics are separated, dried over MgSO4, filtered and the solvent removed in vacuo. The intermediate is obtained by flash column chromatography (silica, eluent dichloromethane). The resulting product is then dissolved in MeOH (1 L). NaOAc (46.1 g), hydroxylamine hydrochloride (29.1 g) are added and the reaction mixture is stirred at room temperature for 2.5 hours. The reaction mixture is quenched with 0.1M NaOH, extracted into DCM (2×), dried over MgSO4, filtered and the solvent removed in vacuo to give the title compound. 1H nmr (CDCl3, 400 MHz); 6.20 (m, 3H), 3.75 (br s, 2H), 1.4 (s, 9H).

1. customThe reaction mixture is flushed with argon, Pd2(dba)3 (5.4 g)
2. additionis added
3. customThe reaction mixture is quenched with water
4. customThe organics are separated
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customthe solvent removed in vacuo
8. customThe intermediate is obtained by flash column chromatography (silica, eluent dichloromethane)
9. customThe reaction mixture is quenched with 0.1M NaOH
10. extractionextracted into DCM (2×)
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. customthe solvent removed in vacuo