Reacción #2336516

Ecuación de reacción

methyl 3-hydroxypicolinate

bromine

Ether

→

methyl 6-bromo-3-hydroxypicolinate

Rendimiento 70.7%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroover a 30 minute
2. 2
   workup.ADDITIONAfter the addition
3. 3
   workup.WAITwas continued for an additional hour
4. 4
   workup.STIRRINGstirring
5. 5
   workup.DISSOLUTIONhad dissolved
6. 6
   OtroThe organic layer was separated
7. 7
   Extracciónthe aqueous phase extracted with ether (200 mL)
8. 8
   Secadodried (MgSO4)
9. 9
   Otrothe solvent evaporated

Procedimiento

To a mechanically stirred solution of methyl 3-hydroxypicolinate (30.6 g) in water (800 mL) was slowly added bromine (32 g) over a 30 minute period. After the addition was complete, stirring was continued for an additional hour. Ether (300 mL) was added and stirring continued until all the solids had dissolved. The organic layer was separated and the aqueous phase extracted with ether (200 mL). The organic phases were combined, dried (MgSO4) and the solvent evaporated to give 32.8 g of methyl 6-bromo-3-hydroxypicolinate as an off-white solid. Recrystallization from methanol/water gave an analytical sample, m.p. 115-117° C.

Fuente