{ 154 ) 



the NH^-gronp was then eliminated by means of amyhiitrite with 

 addition of finely divided copper. 



/;. Starting from 4-6-dibromo-2-amido-//i-xylene prepared according 

 to AuwERS ^), we also obtain 2-4-6-tribromo-?/i-xylene m.p. 85° by 

 replacing the NH^ by Br according to Sandmeyek. 



c. Acetoxylidide 1-3-4 yields on treatment with bromine and water 

 dibromoacetoxylidide '). If this is boiled with hydrochloric acid, so 

 that the acetyl gronp is eliminated and if in the dibromoxylidine so 

 obtained the NH,-groiip is replaced by bromine 2-4-6-tribromo-7/i- 

 xylene is also obtained. 



CHs CH3 CH3 



Br/\Br Bi/Xbi- Bi>/\Br 



I I -» I 05° I -» 85° I 



\ /CH3 \/CH3 \/^"' 



NH NH2 Br 



CO 



CH3 



4. a. In order to arrive at 4-5-6-tribromo-???,-xylene 4-6-dibromo- 

 2-amido-7/i-xylene was converted by means of bromine into 4-5-6- 

 tribromo-/?i-xylidine and from this substance the NH,- group was 

 eliminated by diazotation and boiling with alcohol. 



CII3 



Br/\NII, 



1 120° I 

 \ /CII3 



Br Br Br 



b. Starting from 6-bromo-4-amido-//i-xylene m.p. OG*^ we obtain 

 by bromination 5-6-dibromo-4-amido-»i-xylene m. p. 35°, which is 

 converted by means of the Sandmeyer reaction into 4-5-6-tribromo- 

 ï?i-xylene. 



5. After many failures to prepare it differently, 2-4-5-tribromo-w- 

 xylene was finally made in the following manner. 



