反应 #828711

反应方程式

HCl

Hydrogen

borane methyl sulfide

cyclohexene

→

title product

收率 75.0%

Dicyclohexylchloroborane

收率 75.0%

溶剂

ether

diethyl ether

diethyl ether

反应条件

后处理

1. 1
   其他A 500-mL round-bottom flask capped with a rubber septum, a magnetic stirring bar, and a connecting tube
2. 2
   温度The flask was cooled in an ice bath
3. 3
   其他Dicyclohexylborane precipitated as a white solid
4. 4
   其他The supernatant liquid was removed by a double-ended needle
5. 5
   洗涤the solid was washed with ether
6. 6
   其他the liquid was removed
7. 7
   其他A clear solution was obtained
8. 8
   workup.DISTILLATIONDistillation

实验过程

A 500-mL round-bottom flask capped with a rubber septum, a magnetic stirring bar, and a connecting tube attached to a mercury bubbler was charged with diethyl ether (150 mL) and cyclohexene (41 mL, 400 mmol). The flask was cooled in an ice bath, borane-methyl sulfide (BMS, 20 mL, 200 mmol) was added slowly, and stirring was continued for 3 h at 0° C. Dicyclohexylborane precipitated as a white solid. The supernatant liquid was removed by a double-ended needle, the solid was washed with ether, and the liquid was removed. Then the solid was suspended in 100 mL of diethyl ether, and anhydrous HCl in ether (66.7 mL of 3M solution, 200 mmol) was added slowly to the suspension at 0° C. Hydrogen is rapidly evolved and should be safely vented. A clear solution was obtained. The 11B NMR analysis of the resulting solution showed formation of Chx2BCl (δ 66 ppm in diethyl ether). Distillation provides the pure title product (δ 76 ppm in hexane), 31.6 g, 75% yield, bp 95°-96 ° C. (0.35 mm).

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