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

HRID 1842391Notes

Reaction equation

HRID 1842391 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 21.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2,2-dimethyl-5-(pyridin-4-yl)furan-3(2H)-one (0.81 g, 4.28 mmol) in CHCl3 (20 mL), NBS (1.3 g, 7.28 mmol) was added portionwise at RT. The reaction mixture was then stirred for 2 h and diluted with DCM (100 mL). The organic layers were washed with water (50 mL) and brine (50 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 (0.25 g, 21%) as a solid.

Workup

  1. washThe organic layers were washed with water (50 mL) and brine (50 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-f6b5d30faa754e589dc451f3fb069742
Source dataset
uspto-grants-2015_02
Patent number
US08946222B2

Reaction notes

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