Benzoyl bromide

Remarkably, balogeti-magnesium exdiatige can also be extended to aryl and beteroaryl bromides [24, 25]. Tlius, tlie functionalized aryl bromides 28 and 29 iSdieme 2.7) were converted, at 0 C and at -30 C, respectively, into tlie corte-sponding Grignatd reagents. After treatment witli CuCN, tlie copper derivative 30 and 31 were obtained. Subsequent treatment witli typical electropb des sudi as benzoyl bromide or aliyl bromide fiirnisbed tlie products 32 and 33, in 70 and 8096 yields. 

The action of 2-(bromomethyl)benzoyl bromide on thioamides results in the formation of 2,4-benzothiazepin-5(l/7)-ones l.47... 

Successive treatment of 2-(bromomethyl)benzoyl bromide with ammonium thiocyanate and a secondary amine gives the acylthioureas 2, which cyclize in the presence of sodium carbonate to the 3-(disubstituted amino)benzothiazepinones 3.47... 

The direct chemical evidence clearly indicates that either (26) or (27) can be involved depending on the circumstances. Thus in the benzoylation of toluene, the same mixture of products (1 % m-, 9% o-and 90% p-) is obtained no matter what the Lewis acid catalyst is, and with either benzoyl chloride or benzoyl bromide, though the reaction rates do of course differ this suggests a common attacking... 

Benzotrifluoride Benzoyl bromide Benzoyl chloride Benzoyl iodide 4-Benzphenanthrene Benzyl acetate... 

Similarly benzoyl bromide yields the expected bromo-oxadiazole. Treatment with PClg or PBrs followed by steam distillation also produces the chloro or bromooxadiazoles respectively (T iS). The same reactions have also been carried out with the correspondig -toluyl derivative of glyoxime (4). 

Ligand exchange reactions between [Fe6Mo2S8(SEt)c>]3 or [Fe7Mo2S8(SEt)i2]3 anions and thiols, acetyl chloride, benzoyl chloride, benzoyl bromide or phenol have shown that the... 

With 5-33.3 vol.% water/acetone mixtures, it is found136 that common-ion salts have no effect on the rate of hydrolysis of benzoyl chloride whereas the rate in 15% (but not 33.3%) water is increased by the addition of neutral salts such as lithium bromide or potassium nitrate. The increase in ionic strength on the addition of neutral salts is not the major reason for the increase in rate and nucleophilic catalysis via the more easily hydrolysed benzoyl bromide was postulated. 

Benzoylation of benzoylmethylene triphenylarsorane (20) with benzoyl bromide gave a kinetically controlled acylated product, which on treatment with sodium acetate in chloroform afforded thermodynamically controlled dibenzoylmethylene triphenylarsorane (21) (56). Acylation with carbonic acid anhydride (32, 56), phenylisocyanate (32), or chloroformic ester (32) gave in no case O-acylated product. Similarly, reaction with acetic anhydride afforded l,3-dioxo-l-phenyl-butylidene-(2)-triphenylar-sorane (56). 

Die Reaktion verlauft bei optisch aktivem Ethan-selenophosphonsaure-O-ester unter Inversion. Optisch aktiver Ethan-selenophosphonsaure-O-ethylester reagiert auch mit Acetyl- bzw. Benzoyl-bromid in Diethylether in Gegenwart von Triethylamin zum optisch aktiven (Ethan-selenophosphonsaure-O-ethylester)-Essigsaure (bzw. Benzoesdu-re)-O-Anhydrid (47 bzw. 76%)lOOS ... 

A similar synthesis can be used to generate DBr from benzoyl bromide if it is desired to study DBr and HBr in addition or as an alternative to DCl and HCl. In fact, if an equimolar mixture of the benzoyl halides is used along with D2O, which is about 95 percent D, the product mix will contain all isotopic forms with reasonable intensity ratios for an infrared scan of aU four species in a single ceU. Such a mixture can also be used for the determination of equilibrium constant Kp for the H D exchange reaction... 

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