N-bromobutanimide → 4-bromo-5-(3-chloro-4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one

HRID 1776365Notes

Reaction equation

HRID 1776365 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12](=[O:17])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C1C(=O)N([Br:25])C(=O)C1>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:25][C:11]1[C:12](=[O:17])[C:13]([CH3:15])([CH3:16])[O:14][C:10]=1[C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 593548485-(3-chloro-4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one

Product 1

HCID 593547584-bromo-5-(3-chloro-4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-oneYield 37%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of afford 5-(3-chloro-4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (0.7 g, 2.77 mmol) in CHCl3 (10 mL), NBS (0.84 g, 4.72 mmol was added portionwise at RT. The reaction mixture was then stirred for 1 h. and diluted with DCM (20 mL). The combined organic layers were washed with water (5 mL) and 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-5-(3-chloro-4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (340 mg, 37%) as a thick syrup.

Workup

  1. washThe combined organic layers were washed with water (5 mL) and 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-28270f37042c4a0dbf8e3c33f5f10245
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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