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

HRID 1798671Notes

Reaction equation

HRID 1798671 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11](=[O:16])[CH:10]=2)=[CH:5][CH:4]=1.C1C(=O)N([Br:24])C(=O)C1>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:24][C:10]1[C:11](=[O:16])[C:12]([CH3:14])([CH3:15])[O:13][C:9]=1[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 145333195-(4-Methoxyphenyl)-2,2-dimethylfuran-3(2H)-one

Product 1

HCID 593547994-bromo-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-oneYield 65%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (5.5 g, 0.025 mol) in CHCl3 (100 mL) was added NBS (6.733 g, 0.038 mol) portion wise at RT. The reaction mixture was stirred for 2 h at RT. The reaction mixture was diluted with DCM (100 mL), washed with water (50 mL), brine (50 mL), dried over Na2SO4, filtered and then concentrated in vacuo to obtain the crude product. The crude material was purified via by flash column chromatography using 25% ethyl acetate in hexane and silica gel (230-400 Mesh) to afford 4-bromo-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (4.6 g, 65%) as a solid.

Workup

  1. washwashed with water (50 mL), 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 by flash column chromatography

Sources & evidence

ORD record
ord-460046285efa417ca5b6774933c605bf
Source dataset
uspto-grants-2013_01
Patent number
US08343973B2

Reaction notes

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