Water → 2-Bromo-6-(bromomethyl)pyrazine

HRID 1399980Notes

Reaction equation

HRID 1399980 reaction equation
[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH3:8])[N:3]=1.C1C(=O)N([Br:16])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][Br:16])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 263703042-Bromo-6-methylpyrazine

Product 1

HCID 866968952-Bromo-6-(bromomethyl)pyrazine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 2-bromo-6-methyl-pyrazine (3.0 g, 17.31 mmol) in CCl4 (25 mL) was added NBS (4.60 g, 26.01 mmol) and AIBN (0.248 g, 1.734 mmol) at RT. The mixture was stirred at 55° C. for 48 h. H2O was added followed by extraction with EtOAc (3×100 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified over silica eluting with 5% EtOAc:Hexane to obtain i (1.40 g, 32%). 1H NMR (CDCl3, 400 MHz): δ 8.64 (s, 1H), 8.62 (s, 1H) and 4.50 (s, 2H).

Workup

  1. extractionfollowed by extraction with EtOAc (3×100 mL)
  2. washThe combined organics were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified over silica eluting with 5% EtOAc
  6. customHexane to obtain i (1.40 g, 32%)

Sources & evidence

ORD record
ord-a1741c78ce114e5ebf9e8852515d2690
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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