2-Nitrotoluene → alpha-Bromo-2-nitrotoluene
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10])([O-:3])=[O:2].C(Cl)(Cl)(Cl)Cl.O.[Br:17]Br>>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][Br:17])([O-:3])=[O:2]Participants
Procedure
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.
Sources & evidence
- ORD record
- ord-bfd0ff083e8040ba991d0803126b7b09
- Source dataset
- uspto-grants-1979_08
- Patent number
- US04165268
Reaction notes
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