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

HRID 216980Notes

Reaction equation

HRID 216980 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>ClCCl.CC(N=NC(C#N)(C)C)(C#N)C>[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 96.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Methyl 5-bromo-3-methylpicolinate (800 mg) in dichloromethane (5 mL) was treated with N-bromosuccinimide (619 mg) and AIBN (14.28 mg). The mixture was stirred and irradiated with a 500 W halogen lamp for 3.5 h. The reaction mixture was cooled and diluted with dichloromethane, and washed with water. The organic layer was dried over magnesium sulfate, filtered and evaporated to afford the sub-titled compound (1036 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-b06c4962fa8f42989530d67472629e5c
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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