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

HRID 1842385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842385
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-61af2bab0f8749e98a5437b0682ff497
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946222B2

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