302
S. Sayyahi, J. Saghanezhad / Chinese Chemical Letters 22 (2011) 300–302
40 min. Table 1 shows the scope and limitations of these nucleophilic substitution reactions using several
a-bromoacetophenone derivatives.
The formation of products can be easily detected by the characteristic 13C absorption band of –SCN group for
phenacyl thiocyante at ꢀ112 and a-carbon in phenacyl azide and iodide that shift from ꢀ30 in phenacyl bromide to ꢀ
54 and ꢀ1.3 ppm, respectively. Although phenacyl thiocyantes, azides and iodides were obtained in high isolated
yields, phenacyl cyanides could only be obtained in moderate yields; because the reaction system becomes pasty so
hindering the completion of the reactions. These results are in agreement with the hard and soft acid and base principle
(HSAB) and the data acquired by Sukata for alkyl halides [18].
To evaluate the efficiency of this method for the scaling up experiment, transformation of 1-(4-methoxyphenyl)-2-
bromide was also performed on a 100 mmol scale. Gratifyingly, the substrate provided the corresponding phenacyl
derivatives without appreciable decrease in the yields.
In conclusion, we have reported here the use of tetrabutylammonium bromide as an efficient catalyst in the
synthesis of phenacyl derivatives in water. The reactions generated the corresponding products under mild conditions
and with satisfactory yields.
Acknowledgment
Partial support for this work by Islamic Azad University, Mahshahr branch research council is gratefully
acknowledged.
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