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

HRID 1798671Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798671
[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-460046285efa417ca5b6774933c605bf
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343973B2

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