N-bromobutanimide → HCID 59354807, compound

HRID 1776329Notes

Reaction equation

HRID 1776329 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10](=[O:15])[CH:9]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:23])C(=O)C1>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:23][C:9]1[C:10](=[O:15])[C:11]([CH3:13])([CH3:14])[O:12][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 144923435-(4-Chlorophenyl)-2,2-dimethylfuran-3(2H)-one

Product 1

HCID 59354807HCID 59354807, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To stirred solution of crude 5-(4-chlorophenyl)-2,2-dimethylfuran-3(2H)-one (2.1 g, 13.0 mmol) in CHCl3 (15 mL), NBS (3.93 g, 22.10 mmol) was added portionwise at RT. The reaction mixture was stirred for 1 h and then diluted with DCM (100 mL). The combined organic layers were washed with water (50 mL) and brine (30 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-5-(4-chlorophenyl)-2,2-dimethylfuran-3(2H)-one (2.0 g, 51% over three steps) as an off-white solid.

Workup

  1. additionwas added portionwise at RT
  2. washThe combined organic layers were washed with water (50 mL) and brine (30 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-d0aade1915934aae8ee4353f8d6c43df
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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