Bromine → Methyl 6-amino-3,5-dibromopicolinate

HRID 1271698Notes

Reaction equation

HRID 1271698 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([Br:12])=[CH:4][CH:3]=1.[Br:13]Br>C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([Br:12])=[CH:4][C:3]=1[Br:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 10657127Methyl 6-amino-3-bromopyridine-2-carboxylate

Product 1

HCID 10495131Methyl 6-amino-3,5-dibromopicolinate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of methyl 6-amino-3-bromopyridine-2-carboxylate (20.62 g) (T. R. Kelly and F. Lang, J. Org. Chem. 61, 1996, 4623–4633) in chloroform (570 ml) was treated dropwise over 2 hours with bromine (4.62 ml) in chloroform (115 ml) and stirred 16 hours. The solution was washed with excess aqueous sodium bicarbonate, dried and evaporated. Crystallisation from EtOAc/hexane gave a solid (13.5 g).

Workup

  1. washThe solution was washed with excess aqueous sodium bicarbonate
  2. customdried
  3. customevaporated
  4. customCrystallisation from EtOAc/hexane

Sources & evidence

ORD record
ord-969f8afdac3340dfa25a62aa19e8cfc9
Source dataset
uspto-grants-2007_04
Patent number
US07205408B2

Reaction notes

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