反应详情

温度

0 °C

5-(6-Bromo-2-phenylquinolin-3-yl)pentanoic acid (1A, 4.00 g, 10.4 mmol) was dissolved in DCM (100 mL). The flask was cooled to 0° C. in an ice/water bath before TFAA (14.7 mL, 104 mmol) was slowly added. After stirring at 0° C. for 1 h, tBuOH (29.9 mL) was gradually added and the reaction mixture was allowed to warm to RT overnight. The mixture was diluted with DCM and sat. Sodium bicarbonate. The biphasic solution was separated and the aqueous layer was extracted with DCM (3×). The combined organic phase was dried over anhydrous sodium sulfate and concentrated. Chromatography (5-100% EtOAc/hexanes) afforded tert-butyl 5-(6-bromo-2-phenylquinolin-3-yl)pentanoate (18, 3.71 g; Yield=81%, LCMS (M+H)=440).

1. additionwas slowly added
2. temperatureto warm to RT overnight
3. customThe biphasic solution was separated
4. extractionthe aqueous layer was extracted with DCM (3×)
5. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
6. concentrationconcentrated