Reaction #2336516

Reaction equation

methyl 3-hydroxypicolinate

bromine

Ether

→

methyl 6-bromo-3-hydroxypicolinate

Yield 70.7%

Solvents

water

Conditions

Workup

1. 1
   Otherover 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
   OtherThe organic layer was separated
7. 7
   Extractionthe aqueous phase extracted with ether (200 mL)
8. 8
   Dryingdried (MgSO4)
9. 9
   Otherthe solvent evaporated

Procedure

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.

Source