•Discuss at what stage in the purification you removed each of the following com
ID: 512906 • Letter: #
Question
•Discuss at what stage in the purification you removed each of the following compounds from your reaction mixture. Briefly justify your answer. a) unreacted aryl bromide b) tetrabutylammonium bromide c) the palladium catalyst d) potassium carbonate •Discuss at what stage in the purification you removed each of the following compounds from your reaction mixture. Briefly justify your answer. a) unreacted aryl bromide b) tetrabutylammonium bromide c) the palladium catalyst d) potassium carbonate
This is for a Suzuki reaction with the equation pictured (attached). Thanks!!! Any additional explanation would be greatly appreciated, I really don't understand what is meant by the stages of purification in this reaction...
HO HO Pd(oAc2 (catalytic) Bu4NBr K2CO3, water
Explanation / Answer
after completeing the reaction, organic solvent like ethyle acetate or chloroform added. Excess water was addes to the reaction mixture so that salts like tetrabutyl ammonium bromide and bases K2CO3 dissolve freely in water,. Product and excess aryle bromide will be soluble in organic layer. The metal (Palladium(0)) will not be soluble in any solvent so we can remove it by simple filtration. By separating org layer from water, we can get product and aryl bromide in organi solvent. By simple coloumn purification/ silica coloum we can separate product and aryle bromide. by hexane as eluent on silica coloumn, product elute first as it is more non polar than starting material. At the end, aryl bromide will be eluted.
SO by filtration metal can be removed
By aquous work up, salt and base can be removed
And by coloumn chromatography, product and aryle bromides can be separated
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