Series of substituted Bromanilines. 
353 
after prolonged heating with large excess of methyl iodide the 
trimethyl compound was detected. The isolation of the trimethyl 
compound from the other products of the reactions was readily 
effected ; it is so very sparingly soluble that on cooling a hot 
alcoholic solution it crystallises out almost completely. 
This replacement of alkyl radicals by methyl appears to be 
again due to the dissociation of ammonium salt into amine and 
alkyl iodide and the subsequent separation of the least soluble 
product. Thus : 
C 6 H 4 Br . (Ch|. 2 C 2 H 5 . NI Z C B H 4 Br . (CH 3 ) 2 N + C 2 H 5 I 
C 6 H 4 Br . (CH 3 ) 2 N + CH 3 I X C 6 H 4 Br . (CH 3 ) 3 NI 
Each of the following five compounds were found in this way 
to give y)-bromphenyl trimethyl ammonium iodide : 
C 6 H 4 Br . (CH 3 ) 2 . C 2 H s . NI m. p. 1 89° 0. 
C 6 H 4 Br . (CH 3 ) 2 . C 3 H 7 (n) NI m. p. 1 70° C. 
C 6 H 4 Br . (CH 3 ) 2 . C 3 H 7 (iso) NI m. p. 1 67° C. 
C 6 H 4 Br . (CH 3 ) 2 . C 4 H 9 (iso) NI m. p. 1 67° C. 
C 6 H 4 Br . (CH 3 ) 2 . C 5 H n (iso) NI m. p. 176° C. 
The melting-point of this bromphenyl trimethyl ammonium 
iodide was 200° C., and in every other respect it resembled the 
compound obtained by the addition of methyl iodide to dimethyl 
j?-bromaniline. Consequently the bromine atom is in the para 
position. Since each of the above series of five ammonium salts 
gives rise to para-bromphenyl trimethyl ammonium iodide on 
heating with methyl iodide, they are all para-compounds. They 
were obtained by the addition of methyl iodide to the correspond- 
ing bromanilines ; consequently in the latter also the bromine 
atom is in the para position. 
