PREPARATION OF ARYL CHLORIDES FROM PHENOLS
PREPARATION OF ARYL CHLORIDES FROM PHENOLS
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DOI：
10.1021/jo00297a087
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发表时间：
1990-05-11
影响因子：
3.6
通讯作者：
LEONEBAY, A
中科院分区：
文献类型：
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作者：
BAY, E;BAK, DA;LEONEBAY, A
(2)2对于我们的氯化反应的发生不是必需的，因为PPTC也会氯化非芳香醇。表II列出了各种醇，它们不是酚，但在用PPTC处理时确实经历了氢氧化物被氯化物置换。表II所述的反应比它们的酚类反应更容易发生，这些过程的一般方法如下。将氯气（10 mM）鼓泡到苯基二氯化磷（10 mM）在氯仿（20 mL）中的溶液中。有时需要外部冷却以在整个氯添加过程中保持反应温度低于35 ℃。然后在室温或低于室温下加入醇（10 mM）（表II），并将反应混合物保持在表II中规定的条件下。当反应完成时，将混合物倒入冰/水（50 mL）中并用50%氢氧化钠水溶液中和。分离各层，用两份30 mL氯仿萃取水性部分。将合并的有机萃取物用盐水洗涤，经无水硫酸镁干燥，并浓缩。
(2) 2 is not essential for our chlorination reaction to occur because PPTC will also chlorinate nonaromatic alcohols. Table II lists a variety of alcohols that are not phenols but do undergo hydroxide replacement by chloride upon treatment with PPTC. The reactions described by Table II occur more readily than their phenolic counterparts, and a general method for these processes follows. Chlorine gas (10 mM) is bubbled into a solution of phenylphosphorus dichloride (10 mM) in chloroform (20 mL). External cooling is sometimes necessary to keep the reaction tem-perature below 35 C throughout the chlorine addition. The alcohol (10 mM) is then added at or below room temperature (Table II), and the reaction mixture is maintained at the conditions specified in Table II. When the reaction is complete, the mixture is poured onto ice/water (50 mL) and neutralized with 50% aqueous so-dium hydroxide. The layers are separated, and the aqueous portion is extracted with two 30-mL portions of chloroform. The combined organic extracts are washed with brine, dried over anhydrous magnesium sulfate, and