4-bromo-m-xylene

Bromo-m-xylene General Procedure for Bromination of Polymethylbenzene... 

The products mixture was filtered, and the spent and unused reagent were washed with carbon tetrachloride (30 ml). The solvent was evaporated from the combined filtrate under reduced pressure, and the residue was distilled under vacuum to give 3.6 g (86 %) of 4-bromo-m-xylene. Bp 89-91 °C/14 Torr (lit. 203°C (ref. 16)). 

Tris-(4-iw-xylyl)stibine 514 4-Bromo-m-xylene (56 g) and antimony trichloride (23 g) are dissolved in dry benzene (150 ml), and then metallic sodium (50 g in pieces) is added. When the reaction is complete (usually after warming) the solution is set aside overnight and then filtered. The residue is extracted three times with boiling benzene. All the liquids are united and the benzene is removed, whereafter the oily residue is poured into anhydrous ethanol. In a few minutes the stibine separates as long needles (25 g, 57 %). 

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