m-Chloroperbenzoic acid → 5-Bromo-2-chloro-4-methylpyridine 1-oxide

A solution of 5-bromo-2-chloro-4-methylpyridine (1.0 eq.) and meta-chloroperbenzoic acid (mCPBA) (2.5 eq.) in chloroform (0.1 M) was stirred at 50° C. overnight. After cooling to room temperature, Ca(OH)2 (2.5 eq.) was added to the reaction mixture. The precipitate was filtered and washed with 5% methanol in dichloromethane and ethyl acetate. The filtrate was washed with saturated aqueous Na2S2O3 solution and saturated aqueous NaHCO3 solution. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo into a pale solid that was carried onto the next step without further purification.

1. filtrationThe precipitate was filtered
2. washwashed with 5% methanol in dichloromethane and ethyl acetate
3. washThe filtrate was washed with saturated aqueous Na2S2O3 solution and saturated aqueous NaHCO3 solution
4. washThe combined organic layers were washed with brine
5. dry with materialdried over anhydrous MgSO4
6. concentrationconcentrated en vacuo into a pale solid
7. customthat was carried onto the next step without further purification

ORD record

ord-badf5709df9e4246a156485e9b48678b

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466167B2