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

HRID 1776309Notes

Reaction equation

HRID 1776309 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 22%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a room temperature, 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. The reaction mixture was then stirred for 2 h and diluted with DCM (100 mL). The combined 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, 22%) as a solid.

Workup

  1. additionwas added portionwise
  2. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto obtain the crude product
  7. customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-ca6d2561063b49779127fb0555367277
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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