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

HRID 1778738Notes

Reaction equation

HRID 1778738 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.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 92.5%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 6344DichloromethaneSolvent

Procedure

Methyl 5-bromo-3-methylpyridine-2-carboxylate (800 mg, 3.5 mmol)(Combi-Blocks Cat. No. SS-3016) in methylene chloride (15 mL) was treated with N-bromosuccinimide (620 mg, 3.5 mmol) and AIBN [2,2′-azobis(isobutyronitrile)] (14 mg, 0.087 mmol). The mixture was stirred and irradiated with a 250W tungsten halogen lamp overnight. LCMS showed most starting material was consumed. The mixture was concentration under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (1.0 g). LCMS (M+H)+=309.9.

Workup

  1. customwas consumed
  2. concentrationconcentration under reduced pressure
  3. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

Sources & evidence

ORD record
ord-6b298ea01f154140b9c88ec270691f9b
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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