230 PROCEEDINGS OF THE AMERICAN ACADEMY 



Chlor AND Brombenzofhknones. 



After we had succeeded in effecting the synthesis of the nitro- 

 phenones from the anhydrides, as above described, we concluded to 

 extend the research to the corresponding halogen bodies. We found 

 that, with the exception of the orthobrorn derivative, the reaction 

 takes place in precisely the same manner. 



Orthobrombenzoic anhydride, prepared as stated in the previous 

 paper, was heated in a sealed tube with an equivalent amount of phos- 

 phorpentoxide, and a considerable excess of benzol for four to five 

 hours at 190 to 200°. The product was worked up as described under 

 the nitrophenone, but without result. We were unable to obtain even 

 a trace of brombenzoic acid, the only tangible product being a very 

 small quantity of a yellowish oil, which could not be brought to crystal- 

 lization. The operation we have repeated with varying quantities of 

 the different factors, and varying times of heating, but without suc- 

 cess. It will be remembered, in this connection, that in the case of 

 the orthonitrophenone the course of the reaction left much to be 

 desired, though we finally succeeded in obtaining enough product for 

 analysis. 



Metabrombenzoplienone. 



This body was prepared from metabrombenzoic anhydride, m.pt. 97°, 

 by heating it in a sealed tube with phosphorpentoxide and benzol, and 

 working up the product as described under the nitro compound. It 

 crystallizes from alcohol in colorless needles, which melt at 74°, and 

 dissolve readily in ether, chloroform, and benzol, less easily in alcohol 

 and ligroine. The analyses gave as follows : — 



0.2009 gr. substance gave 0.4401 gr. CO ? and 0.0661 gr. H 2 C- 

 0.1939 gr. gave 0.1390 gr. AgBr. 



Calculated for 

 r ,t | (l)Br Found. 



^ H * 1 (3) C0C c H B . 



C 59.77 59.75 



H 3.45 3.66 



Br 30.66 30.51 



Parabrombenzophenone. 



From parabrombenzoic anhydride, m.pt. 212-213°, by heating to 

 190-200° with phosphorpentoxide and benzol. Crystallizes from 



