N-bromobutanimide → Methyl 5-bromo-3-(bromomethyl)pyridine-2-carboxylate

HRID 339983Notes

Reaction equation

HRID 339983 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:1][C:2]1[CH:3]=[C:4]([CH2:12][Br:13])[C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 45789787Methyl 5-bromo-3-methylpicolinate

Product 1

HCID 58171990Methyl 5-bromo-3-(bromomethyl)pyridine-2-carboxylateYield 49%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 5-bromo-3-methylpyridine-2-carboxylate (1.01 g, 4.39 mmol) in carbon tetrachloride (30.0 mL) was added N-bromosuccinimide (8.60E2 mg, 4.83 mmol) and 2,2′-azo-bis-isobutyronitrile (14.4 mg, 0.0877 mmol). The reaction mixture was stirred at 80° C. for 5 h. The reaction mixture was filtered and the filtrate was concentrated to afford 0.66 g (49% yield) of the desired product.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-dc3f77488259432193e4233a0fc00180
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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