N-bromobutanimide → 4-bromo-2,2-dimethyl-5-(pyridin-4-yl)furan-3(2H)-one

HRID 1776371Notes

Reaction equation

HRID 1776371 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6](=[O:7])[CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[O:3]1.C1C(=O)N([Br:22])C(=O)C1>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:22][C:5]1[C:6](=[O:7])[C:2]([CH3:14])([CH3:1])[O:3][C:4]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 593547902,2-dimethyl-5-(pyridin-4-yl)furan-3(2H)-one

Product 1

HCID 593548244-bromo-2,2-dimethyl-5-(pyridin-4-yl)furan-3(2H)-oneYield 65.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2,2-dimethyl-5-(pyridin-4-yl)furan-3(2H)-one (1.3 g, 6.80 mmol) in CHCl3 (13 mL) was added NBS (2.08 g, 11.6 mmol) portionwise at RT and the reaction mixture was stirred for 3 h. The reaction mixture was diluted with DCM (30 mL), washed with water (10 mL), brine (10 mL), dried over Na2SO4, filtered and then concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 4-bromo-2,2-dimethyl-5-(pyridin-4-yl)furan-3(2H)-one (1.2 g) as an oil.

Workup

  1. washwashed with water (10 mL), brine (10 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto obtain the crude product
  6. customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-43724bd46d424eb88e20cb5972acdaed
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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