Development of an Extremely Efficient Oxidative Chlorination Reaction: The Value of Routine Data Collection

作者：Barnwell Neil^*; Cornwall Philip; Horner Daniel; Knott Jason; Liddon John

来源：Organic Process Research & Development, 2010, 14(1): 278-288.

DOI：10.1021/op900241e

This contribution describes the development of fit extremely efficient process for the oxidative chlorination of a benzyl, alkyl thioether to yield an alkylsulfonyl chloride. This process was subsequently run oil >100 kg scale. The product alkylsulfonyl chloride was required as ail intermediate, being used by several drug projects, to prepare sulfonamides. Routine data collection and reaction profiling has led to understanding, which has allowed an alternative reaction pathway to be exploited for the development of a two-step, oxidation-chlorination process. The scope of this new two-step process was briefly examined. The results of this study have allowed us to propose an empirical method for predicting the course of these oxidative chlorination reactions. During these studies we have developed a simple laboratory rig, constructed from inexpensive, readily available equipment, which allows the controlled accurate delivery of known volumes (100s, of milliliters) of chlorine gas at a given rate. In our laboratories, this has made the use of gaseous chlorine a considerably less onerous task. This work is testimony to the fruit which may be borne from attempts to gain process understanding, even of an already high-yielding reaction.

• 出版日期2010-2