Boron tribromide → 7-Bromo-2-(morpholin-4-yl)-benzooxazol-4-ol

HRID 2186449Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2186449
B(Br)(Br)Br.[Br:5][C:6]1[C:14]2[O:13][C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[N:11][C:10]=2[C:9]([O:21]C)=[CH:8][CH:7]=1>ClCCl>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([OH:21])=[C:10]2[C:14]=1[O:13][C:12]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[N:11]2

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 224566577-Bromo-4-methoxy-2-(morpholin-4-yl)-benzooxazole

Produkt 1

HCID 224566467-Bromo-2-(morpholin-4-yl)-benzooxazol-4-olAusbeute 42,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of boron tribromide (25.6 ml of a 1.0M in dichloromethane) was added slowly to a stirred solution of 7-bromo-4-methoxy-2-(morpholin-4-yl)-benzooxazole (4.0 g) in dry dichloromethane (100 ml) under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature for 90 mins. The mixture was partitioned between sodium hydrogencarbonate solution (50 ml) and dichloromethane (100 ml). The organic layer was separated, dried over magnesium sulphate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 30-50% ethyl acetate in heptane afforded the title compound as an off-white solid (1.64 g).

Aufarbeitung

  1. customThe mixture was partitioned between sodium hydrogencarbonate solution (50 ml) and dichloromethane (100 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customPurification by column chromatography on silica eluting with 30-50% ethyl acetate in heptane

Quellen und Nachweise

ORD-Eintrag
ord-398baf3df020478ca80c7f953c69cfc0
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06403791B1

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