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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 13
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Original Articles

Electrochemical Method for the Preparation of Dibromomethyl, Bis(bromomethyl), and Bis(dibromomethyl) Arenes

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Pages 2304-2309 | Received 11 Sep 2008, Published online: 01 Jun 2009
 

Abstract

Electrochemical bromination of alkyl aromatic compounds by two-phase electrolysis yields the corresponding α, α-dibrominated products. The reaction has been carried out in a single-compartment electrochemical cell using aqueous sodium bromide (40–50%), containing a catalytic amount of HBr as electrolyte, and chloroform, containing an alkyl aromatic compound, as the organic phase with a Pt plate as anode at 10–15°C. Two-phase electrolysis results in high yields (70–90%) of dibromomethyl, bis(bromomethyl), and bis(dibromomethyl) arenes, depending upon the charge passed.

Notes

a Structures were confirmed from their spectra (NMR, IR) data.

b Isolated yield.

c p-Nitro bromomethyl benzene (50%) is present along with 50% p-nitro dibromomethyl benzene.

d Isolated as a solid after trituration with n-hexane.

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