N-bromobutanimide → Ethyl 6-(bromomethyl)picolinate

HRID 1162583Notes

Reaction equation

HRID 1162583 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N:7]=1)=[O:5])[CH3:2].C1C(=O)N([Br:20])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][Br:20])[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 564597Ethyl 6-methylpyridine-2-carboxylate

Product 1

HCID 23033755Ethyl 6-(bromomethyl)picolinateYield 98.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 6-methyl-pyridine-2-carboxylic acid ethyl ester (1.65 g, 10 mmol), NBS (1.77 g, 10 mmol), and benzoyl peroxide (100 mg) in carbon tetrachloride (20 ml) was refluxed for 14 h. After cooling to room temperature, the reaction mixture was partitioned between diethyl ether and water (120 ml, 4:1), organic layer was washed with water (2×20 ml), brine, dried (MgSO4), filtered and concentrated to give 6-bromomethyl-pyridine-2-carboxylic acid ethyl ester (2.4 g) which was used without further purification. LCMS m/z: 245 (M+1)+.

Workup

  1. temperaturewas refluxed for 14 h
  2. customthe reaction mixture was partitioned between diethyl ether and water (120 ml, 4:1), organic layer
  3. washwas washed with water (2×20 ml), brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-68468710087740078ac5874558b61ab5
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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