Sodium bromobenzene interaction

Salicyl-u-toluide has been prepared only by the action of phosphorus oxychloride upon a mixture of salicylic acid and o-toluidine. The useful methods of preparation of salicylanilide are by the interaction of salicylic acid and aniline in the presence of phosphorus trichloride, by heating phenyl salicylate and aniline, and from o-hydroxybenzamide and bromobenzene in the presence of small amounts of sodium acetate and metallic copper. A number of these and other anilides have been described. ... 

On the small scale, no reaction occurred on boiling perfluorohexyl iodide in contact with metallic sodium. With 140 g of iodide and 7 g of sodium an explosion occurred after 30 min [6]. The temperature range for smooth interaction of bromobenzene, 1-bromobutane and sodium in ether to give butylbenzene is critical. Below 15°C reaction is delayed but later becomes vigorous, and above 30°C the reaction becomes violent [7]. Sodium wire and chlorobenzene react exothermally in benzene under nitrogen to give phenylsodium, and the reaction must be controlled by cooling. Use of... 

This is formed by the interaction of 30 grams of p-tolyldichloroarsine, 42 grams of bromobenzene, and 24 grams of sodium in 500 c.c. of ether, the reaction commencing spontaneously, and being completed by heating for three days. From alcohol the arsine is deposited in colourless crystals, M.pt. 50° C. the mercurichloride crystallises from glacial acetic acid with M.pt. 147° C., and the platinichloride is a yellow precipitate, M.pt. 288° C. 

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