N-bromobutanimide → Ethyl 2-bromo-2-(pyridin-4-yl)propanoate

HRID 2360260Notes

Reaction equation

HRID 2360260 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:3][CH:2]=1.[Br:14]N1C(=O)CCC1=O>CC#N.CCOCC.C([O-])([O-])=O.[Na+].[Na+]>[Br:14][C:7]([C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 11651240Ethyl 2-(pyridin-4-yl)propanoate

Product 1

HCID 58930190Ethyl 2-bromo-2-(pyridin-4-yl)propanoate

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 10340Sodium CarbonateSolvent

Procedure

The above compounds were prepared according to the procedure reported in the literature: see D. Yang, J. Org. Chem. 2002, 67, 7429. MS: 258, 260 (M+1). To a solution of ethyl 2-(pyridin-4-yl)propanoate (5.3 g, 30 mmol), Mg(ClO4)2 (Aldrich, 2.0 g, 9.0 mmol) in CH3CN (60 mL) was added N-bromosuccinimide (Aldrich, 5.9 g, 33 mmol) at room temperature. After 2 h, the reaction mixture was diluted with ether (200 mL), and 10% Na2CO3. The organic phase was separated, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography. Mass Spec. m/z+ion 258, 260 (M+1).

Workup

  1. customThe above compounds were prepared
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-325ca3bce89d435c887f42c76aab56ab
Source dataset
uspto-grants-2014_04
Patent number
US08686011B2

Reaction notes

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