09 August 2012 (online)
Dedicated to my Supervisor Prof. Rajani Giridhar and thankful to ICMR, New Delhi for financial support.
Bromoacetyl bromide is a versatile and widely used reagent for the synthesis of heterocyclic compounds, especially for the regioselective synthesis of heterocycles. It easily forms esters and amides used for the synthesis of many important intermediates to yield therapeutically active compounds, e.g. cefotetan and labetalol[ 1 ] and is also utilized for the selective cleavage of ethers and acetals and exploited for the selective extension of carbon chains.[ 2 ]
Spectroscopic investigations have shown that bromoacetyl bromide in both gaseous and liquid phases is a mixture of two conformers, anti and gauche in the ratio of 40:60, respectively.[ 3 ]
Bromoacetyl bromide is prepared by reaction of acetic acid and bromine in the presence of red phosphorous at 140 °C.
Bromoacetyl bromide is a colorless corrosive liquid (bp 296.6–302 °C) and hydrolyses readily in water. Some of the important uses of bromoacetyl bromide are depicted below.
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