Reaktion #689968

ord-9ecd94bb63d24f9eb45f6d9f4213f937

Reaktionsgleichung

Cc1nc2ccccc2o1
2-methyl-benzooxazole
O=C1CCC(=O)N1Br
NBS
→
BrCc1nc2ccccc2o1
2-bromomethyl-benzooxazole
Ausbeute 17.0%

Edukte

Cc1nc2ccccc2o1
2-methyl-benzooxazole
O=C1CCC(=O)N1Br
NBS

Reagenzien

O=C(OOC(=O)c1ccccc1)c1ccccc1
benzoyl peroxide

Lösungsmittel

ClC(Cl)(Cl)Cl
CCl4

Reaktionsbedingungen

Temperatur
100°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturthen cooled
  2. 2
    FiltrationSuccinimide was filtered off
  3. 3
    Sonstigethe mixture was evaporated to dryness

Vorschrift

A solution of 35 g (0.263 mol) of 2-methyl-benzooxazole in CCl4 (300 mL) was treated with 47 g (0.263, 1 eq) of NBS and 1 g of benzoyl peroxide. The mixture was refluxed (100° C.) over night then cooled. Succinimide was filtered off and the mixture was evaporated to dryness. Column chromatography yielded 9.2 g (17%) of 2-bromomethyl-benzooxazole as a light yellow oil, MS: 210, 212 (MH+). (H. Uno, M. Kurokawa, Y. Masuda, Chem. Pharm. Bull., 1981, 29, 2359).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07906546B2uspto-grants-2011_03