e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron Letters

Regioselective bromination of activated aromatic substrates with a ZrBr 4/diazene mixture

T Stropnik, S Bombek, M Kočevar, S Polanc

Index: Stropnik, Tadej; Bombek, Sergeja; Kocevar, Marijan; Polanc, Slovenko Tetrahedron Letters, 2008 , vol. 49, # 11 p. 1729 - 1733

Full Text: HTML

Citation Number: 21

Abstract

A regioselective method for the bromination of phenols, ethers and anilines using a ZrBr4/diazene mixture is described. The reaction takes place under mild reaction conditions and the bromine atom adds first at the para unsubstituted position with respect to the OH, OR or NR2 group of the activated aromatic substrate. Less reactive compounds such as toluene, phenyl acetate, benzonitrile and trifluoromethylbenzene remain intact under the same ...

2,4-Dibromophenol Structure

2,4-Dibromophenol

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

~77%

diisopropyl bicarbamate Structure

diisopropyl bic...

2,4,6-Tribromophenol Structure

2,4,6-Tribromophenol

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Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

2,6-Dibromophenol Structure

2,6-Dibromophenol

~79%

diisopropyl bicarbamate Structure

diisopropyl bic...

2,4,6-Tribromophenol Structure

2,4,6-Tribromophenol

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2,5-Dichlorophenol Structure

2,5-Dichlorophenol

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

~87%

2,5-dichloro-4-bromophenol Structure

2,5-dichloro-4-...

diisopropyl bicarbamate Structure

diisopropyl bic...

Learn More

m-Cresol Structure

dead Structure

~71%

Diethyl 1,2-hydrazinedicarboxylate Structure

Diethyl 1,2-hyd...

4-Bromo-3-methylphenol Structure

4-Bromo-3-methy...

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4-Chloro-2-methylphenol Structure

4-Chloro-2-meth...

dead Structure

~0%

Diethyl 1,2-hydrazinedicarboxylate Structure

Diethyl 1,2-hyd...

2-Methyl-4-chloro-6-bromophenol Structure

2-Methyl-4-chlo...

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Anisole Structure

dead Structure

~0%

4-Bromoanisole Structure

Diethyl 1,2-hydrazinedicarboxylate Structure

Diethyl 1,2-hyd...

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4-Bromoaniline Structure

dead Structure

~0%

Diethyl 1,2-hydrazinedicarboxylate Structure

Diethyl 1,2-hyd...

2,4,6-Tribromoaniline Structure

2,4,6-Tribromoa...

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dead Structure

Phenol Structure

~0%

4-Bromophenol Structure

Diethyl 1,2-hydrazinedicarboxylate Structure

Diethyl 1,2-hyd...

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Diphenyl oxide Structure

dead Structure

~0%

Diethyl 1,2-hydrazinedicarboxylate Structure

Diethyl 1,2-hyd...

4,4'-Oxybis(bromobenzene) Structure

4,4'-Oxybis(bro...

Learn More

m-Cresol Structure

dead Structure

~0%

Diethyl 1,2-hydrazinedicarboxylate Structure

Diethyl 1,2-hyd...

4-Bromo-3-methylphenol Structure

4-Bromo-3-methy...

Learn More

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

N,N-Dimethylaniline Structure

N,N-Dimethylaniline

~88%

diisopropyl bicarbamate Structure

diisopropyl bic...

4-Bromo-N,N-dimethylaniline Structure

4-Bromo-N,N-dim...

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4-Chloro-2-methylphenol Structure

4-Chloro-2-meth...

dead Structure

~78%

Diethyl 1,2-hydrazinedicarboxylate Structure

Diethyl 1,2-hyd...

2-Methyl-4-chloro-6-bromophenol Structure

2-Methyl-4-chlo...

Learn More

4-Chloro-2-methylphenol Structure

4-Chloro-2-meth...

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

~73%

diisopropyl bicarbamate Structure

diisopropyl bic...

2-Methyl-4-chloro-6-bromophenol Structure

2-Methyl-4-chlo...

Learn More

4-Bromophenol Structure

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

~0%

2,4-Dibromophenol Structure

2,4-Dibromophenol

diisopropyl bicarbamate Structure

diisopropyl bic...

Learn More

2-Bromophenol Structure

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

~0%

2,4-Dibromophenol Structure

2,4-Dibromophenol

diisopropyl bicarbamate Structure

diisopropyl bic...

Learn More

2,5-Dichlorophenol Structure

2,5-Dichlorophenol

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

~0%

2,5-dichloro-4-bromophenol Structure

2,5-dichloro-4-...

diisopropyl bicarbamate Structure

diisopropyl bic...

Learn More

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

N,N-Dimethylaniline Structure

N,N-Dimethylaniline

~0%

diisopropyl bicarbamate Structure

diisopropyl bic...

4-Bromo-N,N-dimethylaniline Structure

4-Bromo-N,N-dim...

Learn More

2,6-Dichlorophenol Structure

2,6-Dichlorophenol

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

~0%

diisopropyl bicarbamate Structure

diisopropyl bic...

2,6-Dichloro-4-bromophenol Structure

2,6-Dichloro-4-...

Learn More

2,4-Dibromophenol Structure

2,4-Dibromophenol

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

~0%

diisopropyl bicarbamate Structure

diisopropyl bic...

2,4,6-Tribromophenol Structure

2,4,6-Tribromophenol

Learn More

2-Chlorophenol Structure

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

~0%

diisopropyl bicarbamate Structure

diisopropyl bic...

4-Bromo-2-chlorophenol Structure

4-Bromo-2-chlor...

Learn More

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

2,6-Dibromophenol Structure

2,6-Dibromophenol

~0%

diisopropyl bicarbamate Structure

diisopropyl bic...

2,4,6-Tribromophenol Structure

2,4,6-Tribromophenol

Learn More

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

2,4-Dichlorophenol Structure

2,4-Dichlorophenol

~0%

diisopropyl bicarbamate Structure

diisopropyl bic...

2-bromo-4,6-dichlorophenol Structure

2-bromo-4,6-dic...

Learn More

4-Chloro-2-methylphenol Structure

4-Chloro-2-meth...

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

~0%

diisopropyl bicarbamate Structure

diisopropyl bic...

2-Methyl-4-chloro-6-bromophenol Structure

2-Methyl-4-chlo...

Learn More

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

Structure

~0%

diisopropyl bicarbamate Structure

diisopropyl bic...

4-Bromoaniline Structure

Learn More

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

2,4-Dichlorophenol Structure

2,4-Dichlorophenol

~76%

diisopropyl bicarbamate Structure

diisopropyl bic...

2-bromo-4,6-dichlorophenol Structure

2-bromo-4,6-dic...

Learn More

2-Chlorophenol Structure

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

~78%

diisopropyl bicarbamate Structure

diisopropyl bic...

4-Bromo-2-chlorophenol Structure

4-Bromo-2-chlor...

Learn More

4-Bromophenol Structure

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

~88%

2,4-Dibromophenol Structure

2,4-Dibromophenol

diisopropyl bicarbamate Structure

diisopropyl bic...

Learn More

2-Bromophenol Structure

Diisopropyl azodicarboxylate Structure

Diisopropyl azo...

~89%

2,4-Dibromophenol Structure

2,4-Dibromophenol

diisopropyl bicarbamate Structure

diisopropyl bic...

Learn More

Diphenyl oxide Structure

dead Structure

~70%

Diethyl 1,2-hydrazinedicarboxylate Structure

Diethyl 1,2-hyd...

4,4'-Oxybis(bromobenzene) Structure

4,4'-Oxybis(bro...

Learn More

Synthesis, structural characterization, VHPO mimicking perox...

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Bromination of phenols in bromoperoxidase-catalyzed oxidatio...

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Green, mild and efficient bromination of aromatic compounds ...

[Khosravi, Kaveh; Kazemi, Samira Chinese Chemical Letters, 2012 , vol. 23, # 4 p. 387 - 390]

High??Yielding Cleavage of (Aryloxy) acetates

[Spurg, Anke; Waldvogel, Siegfried R. European Journal of Organic Chemistry, 2008 , # 2 p. 337 - 342]

Dinuclear Oxidovanadium (IV) and Dioxidovanadium (V) Complex...

[European Journal of Inorganic Chemistry, , # 35 p. 5377 - 5390]