5-(thiophen-2-yl)-2-p-tolyloxazole was synthesized via an oxidative cyclization reaction between 2-bromo-1-(thiophen-2-yl)-1-ethanone and p-tolylmethanamine in the presence of a catalyst amount of iodine and tert-butyl hydroperoxide (TBHP). The structure of the targeted product was confirmed by Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR) and mass spectroscopy (MS). The results indicated that the optimum synthetic conditions were determined as follows: the amount of 2-bromo-1-(thiophen-2-yl)-1-ethanone, p-tolylmethanamine, iodine, TBHP (mass fraction 55%) and sodium bicarbonate was 1 mmol, 1.3 mmol, 0.2 mmol, 1.2 mmol and 1.0 mmol, respectively, at room temperature for 12 h. The yield of the product reached 89.7 % under the above synthetic condition. The zone of inhibition showed that this compound exhibited a remarkable antibacterial activity against Escherichia coli.