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

HRID 46098Notes

Reaction equation

HRID 46098 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-db7576fa46da4260a610fe041ea2cf0f
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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