N-bromobutanimide → 2-(Bromomethyl)-5-ethoxypyrazine

HRID 715540Notes

Reaction equation

HRID 715540 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[N:8][C:7]([CH3:10])=[CH:6][N:5]=1)[CH3:2].C1C(=O)N([Br:18])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>[Br:18][CH2:10][C:7]1[CH:6]=[N:5][C:4]([O:3][CH2:1][CH3:2])=[CH:9][N:8]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1057582-Methyl-5-ethoxypyrazine

Product 1

HCID 867175972-(Bromomethyl)-5-ethoxypyrazineYield 32%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-ethoxy-5-methylpyrazine (0.86 g, 6.22 mmol), NBS (1.440 g, 8.09 mmol), and diphenylperoxyanhydride (0.151 g, 0.622 mmol) in carbon tetrachloride (20 mL) was heated to 80° 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 ISCO (40 g silica, 40 mL/min, 0-30% EtOAc/Hexanes over 25 min) to afford 2-(bromomethyl)-5-ethoxypyrazine (430 mg, 32%). MS (m/z) 217.0 (M+).

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 ISCO (40 g silica, 40 mL/min, 0-30% EtOAc/Hexanes over 25 min)

Sources & evidence

ORD record
ord-390445fb987e49ddb77db1465298543e
Source dataset
uspto-grants-2015_11
Patent number
US09187464B2

Reaction notes

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