N-bromobutanimide → HCID 18986082, compound

HRID 715542Notes

Reaction equation

HRID 715542 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.C1C(=O)N([Br:16])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][Br:16])[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 27628354-Bromo-2-methylpyridine

Product 1

HCID 18986082HCID 18986082, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromo-2-methylpyridine (2.0 g, 11.63 mmol), NBS (2.69 g, 15.11 mmol), and diphenylperoxyanhydride (0.282 g, 1.163 mmol) in carbon tetrachloride (50 mL) was heated to 100° C. overnight. Cooled to RT, diluted with saturated NaHCO3, and extracted with ethyl acetate (3×). The combined organic extracts were washed with saturated NaCl (2×), dried over Na2SO4, filtered, and concentrated. The residue was purified via silica gel chromatography (ISCO, 120 g silica, 60 mL/min, 0-80% EtOAc/Hexanes over 45 min) to afford 4-bromo-2-(bromomethyl)pyridine (1.05 g, 36%). MS (m/z) 251.9.

Workup

  1. temperatureCooled to RT
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic extracts were washed with saturated NaCl (2×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via silica gel chromatography (ISCO, 120 g silica, 60 mL/min, 0-80% EtOAc/Hexanes over 45 min)

Sources & evidence

ORD record
ord-e2e9907ee16546d487fe873e22d2be56
Source dataset
uspto-grants-2015_11
Patent number
US09187464B2

Reaction notes

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