Water → HCID 66643875, compound

HRID 1474309Notes

Reaction equation

HRID 1474309 reaction equation
[CH:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]#[N:10])=[C:5]([O:11][CH3:12])[CH:4]=1)=[CH2:2].[Br:13]N1C(=O)CCC1=O.[OH2:21]>O1CCOCC1>[Br:13][CH2:2][CH:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]#[N:10])=[C:5]([O:11][CH3:12])[CH:4]=1)[OH:21]

Participants

5

Reactant 3

HCID 962Water2×HCID 67184N-bromobutanimideHCID 66643904HCID 66643904, compound

Product 1

HCID 66643875HCID 66643875, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 6-ethenyl-4-methoxypyridine-3-carbonitrile (80.0 mg, 0.499 mmol) in 1,4-dioxane (8 mL) and H2O (4 mL) was treated with N-bromosuccinimide (89.0 mg, 0.499 mmol, 1.0 equiv). The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was poured into H2O (8 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were washed with saturated aqueous NaCl (1×30 mL), dried over Na2SO4. Evaporation of the solvent gave an oil that was purified over SiO2 (0-30% EtOAc/hexanes as eluent) yielding 6-(2-bromo-1-hydroxyethyl)-4-methoxypyridine-3-carbonitrile.

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. washThe combined organic layers were washed with saturated aqueous NaCl (1×30 mL)
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvent
  5. customgave an oil that
  6. customwas purified over SiO2 (0-30% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-dcf01e69802a42d69c1d35c278156d99
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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