Reaktion #348483

ord-bfd0ff083e8040ba991d0803126b7b09

Reaktionsgleichung

Cc1ccccc1[N+](=O)[O-]
o-nitrotoluene
ClC(Cl)(Cl)Cl.O
carbon tetrachloride water
BrBr
bromine
O=[N+]([O-])c1ccccc1CBr
o-nitrobenzyl bromide
Ausbeute 45.0%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Even the side-chain brominations of o-nitrotoluene in a carbon tetrachloride/water mixture using elementary bromine and under UV-irradiation, which have been described recently in German Democratic Republic patent specifications Nos. 74279 and 82463, provide only o-nitrobenzyl bromide in a yield of 45 to 55%. Continuation of the bromination did not prove advantageous. The process described in German Democratic Republic patent specification No. 118609 affords a somewhat better yield when o-nitrotoluene is brominated in carbon tetrachloride under irradiation with visible or ultra-violet light or using peroxide as catalyst; but in this process too it was not possible to obtain either a benzal bromide or a complete bromination of o-nitrotoluene as starting material to benzyl bromide.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04165268uspto-grants-1979_08