m-Chloroperbenzoic acid → 2-Chloro-5-chloromethylpyridine 1-oxide

To an icecold solution of 2-chloro-5-(chloromethyl)-pyridine (5 g, 29.6 mmol) in DCM (130 mL) was added dropwise a solution of 3-chlorobenzo-peroxoic acid (10.23 g, 59.3 mmol) in DCM (80 mL). The resulting solution was warmed to RT and stirred for 7 d till all starting material was consumed as judged by TLC. After this the reaction mixture was carefully treated with a saturated K2CO3 solution. The resulting precipitate was removed by filtration and the organic layer was washed with a saturated K2CO3 solution and brine. The organic layer was dried, filtered, and evaporated yielding the titled compound as an oil which slowly crystallizes (5.3 g, 90% yield).

1. customwas consumed
2. additionAfter this the reaction mixture was carefully treated with a saturated K2CO3 solution
3. customThe resulting precipitate was removed by filtration
4. washthe organic layer was washed with a saturated K2CO3 solution and brine
5. customThe organic layer was dried
6. filtrationfiltered
7. customevaporated

ORD record

ord-1cb3856570834803a6ba83b8544e3f59

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318793B2