Bromine → 7-bromo-6-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 885932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 885932
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.[Br:13]Br>C(Cl)Cl.C1COCC1>[Br:13][C:3]1[C:2]([CH3:1])=[CH:12][C:6]2[NH:7][C:8](=[O:11])[CH2:9][O:10][C:5]=2[CH:4]=1

Komponenten

5

Edukt 2

HCID 24408BromineHCID 27638392H-1,4-Benzoxazine-3(4H)-one, 6-methyl-

Produkt 1

HCID 671865677-bromo-6-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-oneAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 6-methyl-2H-1,4-benzoxazin-3(4H)-one (10.0 g, 61.3 mmol) in DCM (200 mL) and THF (200 mL) at 0° C. was added bromine (15.0 g, 93.7 mmol) dropwise. The reaction mixture was stirred at this temperature for 30 minutes, then filtered. The solid was washed with Et2O (200 mL) to give the title compound (11.95 g, 80%) as a white solid that was used without further purification. δH (CDCl3) 8.95 (1H, s), 7.16 (1H, s), 6.70 (1H, s), 4.59 (2H, s), 2.31 (3H, s).

Aufarbeitung

  1. filtrationfiltered
  2. washThe solid was washed with Et2O (200 mL)

Quellen und Nachweise

ORD-Eintrag
ord-ea0e1079e26d4915a0a11a58afcdb3f1
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242116B2

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