W-Bromochlorobenzene

Thus o-hydroxyphenyl-llthium cannot be obtained from o-bromophenol and lithium but, under proper conditions, o-bromophenol reacts with -butyl-lithium to give a good yield of the lithium salt of o-hydroxyphenyl-Uthium. An interesting application is to the preparation from w-bromochlorobenzene and -butyl-lithium of w-chlorobenzoic acid— an expensive chemical ... 

Synonym /w-bromochlorobenzene, 3-bromo-l-chlorobenzene, l-bromo-3-chlorobenzene... 

Reduction of 2,6-dibromobenzenediazonium chloride, which would be expected to give w-dibromobenzene, actually yields chiefly w-bromochlorobenzene. How do you account for this ... 

A dry 2-1. three-necked round-bottomed flask is equipped with a sealed stirrer, a 500-ml. dropping funnel (Note 1), and an efficient reflux condenser attached to a calcium chloride tube. In the flask are placed 29.1 g. (1.2 gram atoms) of magnesium turnings, a crystal of iodine, and about 50 ml. of dry ether. A solution of 229 g. (1.2 moles) of w-bromochlorobenzene (Note 2) in 850 ml. of dry ether is added with stirring at a rate which maintains rapid refluxing. The reaction begins after 20-50 ml. of the ether solution is added (Note 3), and the addition requires 1-3 hours. The mixture is stirred and heated on the steam bath under reflux for 1 hour after all the w-bromochlorobenzene has been added. 

If the reaction does not begin spontaneously, the mixture should be heated under reflux until the reaction starts before more than 50 ml. of the w-bromochlorobenzene solution is added. 

Problem 18.31 Using C6H6, C6HsCH3, via diazonium salts and other needed reagents, prepare (a) o-chloroto-luene, (6) m-chlorotoluene, (c) 1,3,5-tribromobenzene, (d) w-bromochlorobenzene, (e) /7-iodotoluene, (/) p-dini-trobenzene and (g) p-cyanobenzoic acid. Do not repeat the synthesis of intermediate products. ... 

A good example of this effect can be seen in the nitration of w-bromochlorobenzene ... 

Bromochlorobenzene, /w-dibromobenzene, and o-bromoanisole are obtained analogously in about 90% yields. In the last case the treatment with H2S04 is omitted. 

CAS 106-39-8 EINECS/ELINCS 203-575-8 Synonyms p-Bromochlorobenzene p-Bromophenyl chloride 1-Chloro-4-bromobenzene 4-Chlorobromobenzene 4-Chloro-1-bromobenzene p-Chlorobromobenzene 4-Chlorophenyl bromide p-Chlorophenyl bromide Empirical C6H4BrCI Properties M.w. 191.46 Toxicology Mutagen TSCA listed Uses Dye intermediate intermediate for haloperidol, loperamide Manuf/Distrib. Morre-Tec Ind. http //www.morretec.com-. Ocean Chems. http //WWW. oceanchemicals. co. uk... 

The toxic effects of hydrocarbons are well established. Injection of 150 mg/kg of bromobenzene into rats produces acute centrolobulm- hepatic necrosis within 48 hours (Koch-Weser el al., 1952). The toxieitj is related to the general nutiitional state, ilethionine and cj stine, or a high protein diet, effectively combat the effects of the hydrocarbons. Koch-Weser suggests the liver damage is due to removal of cysteine and methionine, since p-dibromobenzene and p-bromochlorobenzene, which do not form mercapturic acids, do not cause hepatic lesions while w-chloro-... 

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