A novel effective protocol has been developed for direct fluorination of naproxen using the electrophilic fluorinating reagents 1-chloromethy1-4-fluoro-l,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor™, F-TEDA-BF₄) and N-fluorobenzenesulfonimide (NFSI) in MeCN and H₂O solvents with the formation of 2-(5-fluoro-6-methoxynaphthalen-2-yl)propionic and 2-(5,5-difluoro-6-oxo-5,6-dihydronaphthalen-2-yl)propionic acids. The reaction of naproxen with an excess of Selectfluor (mol. ratio NF-reagent/naproxen = 2.2) in MeOH gives methyl 2-(5,5-difluoro-6,6-dimethoxy-5,6-dihydronaphthalen-2-yl)propionate as the main product. The mechanistic aspects of the reactions and X-ray data of products are discussed.

已开发出一种新的有效协议，用于使用亲电子氟化试剂1-氯甲基1-4-氟-1,4-二氮杂双环[2.2.2]辛烷双（四氟硼酸酯）直接氟化萘普生（Selectfluor™，F-TEDA-BF ₄）和N-氟苯磺酰亚胺（NFSI）在MeCN和H ₂ O溶剂中形成2-（5-氟-6-甲氧基萘-2-基）丙酸和2-（5,5-二氟-6-氧代-5） ，6-二氢萘-2-基）丙酸。萘普生与过量的Selectfluor（摩尔比NF-试剂/萘普生= 2.2）在MeOH中的反应生成甲基2-（5,5-二氟-6,6-二甲氧基-5,6-二氢萘-2-基）丙酸酯为主要产品。讨论了反应的机理和产物的X射线数据。