[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:14]Br>C(Cl)(Cl)Cl>[Br:14][C:2]1[CH:3]=[CH:4][C:5]2[S:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[C:9]=2[CH:1]=1To a stirred, cold solution (0° C.) of 275 g. of dibenzothiophene in 1 liter of chloroform is added over 30 minutes 253 g. of bromine in 500 ml. of chloroform. After sixteen hours of stirring the mixture is heated to its reflux temperature and maintained at reflux for about 30 minutes. The mixture is then evaporated, and 900 ml. of ethanol are added to the residue. The white solid collected by filtration is 2-bromodibenzothiophene, m.p. 112°-116° C.
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