反应详情

温度

0 °C

The starting 4-(ethylthio)benzyl alcohol was prepared as follows. A mixture of lithium aluminum hydride (5.2 g) and tetrahydrofuran (250 mL) was cooled to 0° C. with stirring under N2 atmosphere. A solution of 4-(ethylthio)benzoic acid (25 g) in tetrahydrofuran (300 mL) was added at a rate so as to control H2 evolution. The reaction mixture was then allowed to warm to room temperature and stirred 15 hours. The mixture was cooled in ice and a solution of 15% aqueous sodium hydroxide solution was added, (6 mL) followed by water (21 mL). The mixture was stirred at ice temperature for 1 hour and for 2 hours at ambient temperature. The solution was decanted, diluted with diethyl ether and washed with saturated aqueous NaCl solution. The organic phase was dried over MgSO4, filtered through a celite pad and concentrated to give 4-(ethylthio)benzyl alcohol (20 g). This material was converted to the corresponding bromide as in Example 1 except that diethyl ether and hexane were used for the triturations rather than heptane and petroleum ether, respectively.

1. customThe starting 4-(ethylthio)benzyl alcohol was prepared
2. temperatureto warm to room temperature
3. stirringstirred 15 hours
4. temperatureThe mixture was cooled in ice
5. stirringThe mixture was stirred at ice temperature for 1 hour and for 2 hours at ambient temperature
6. customThe solution was decanted
7. additiondiluted with diethyl ether
8. washwashed with saturated aqueous NaCl solution
9. dry with materialThe organic phase was dried over MgSO4
10. filtrationfiltered through a celite pad
11. concentrationconcentrated