smjp1

here is the edited version of 2,5-bis(4-(diphenylamino) styryl)benzene-1,4-dinitrile-changes in blue. 2 Grignards simultaneously to form 1,4-dietlybenzene __AND__ bromination/elimination to 1,4-styrene after acid steps. This looks good. My only suggestion is that you protect the aromatic amine as an acetamide before nitration. This ensures that it remains an ortho para director, and it avoids possible oxidation reactions. You also might want to brominate and dehydrohalogenate afther the nitriles are on, as these phenylvinyl groups are reactive to both acid conditions and free radicals. It is considered that the CuCN reaction may be free radical mediated, so you might end up with polymer. The logic of the synthesis is quite good Alfred, Katalin and OJ: I The reactions that you have chosen in this are all workable and known reactions. You have clearly researched some advanced steps, such as the Heck type coupling to make the triaryl amines, and the end product. I only have a couple of suggestions. First is that you consider reactivity of some of the groups that you put on early, such as the vinyl group. This is highly reactive toward the acid conditions of the nitration reaction. It may be best to keep these as ethyl groups (simply use bromoethane as the alkylating agent) At the end, it is easy to convert to the alpha bromo compound with NBS, and eliminate to produce the alkene. Second is that, with the symetric molecule, you can do the first grignard reactions simultaneously, and save steps. Really nice start Bruce Bondurant


 * __ ﻿NEW UPLOAD!! __**

This really looks great! Short and sweet. I really don't see any problems in the synthetic plan I especially like your use of the vilsmeier haack reaction Write up a short narative with references to literature, and this post is complete. Bruce Bondurant

__** NARRATION: **__ __﻿__ __**REFERENCES:**__
 * ** __Starting material (I__): 1,4Dibromo-2,5-Diethylbenzene (Sigma Aldrich) **
 * ** Magnessium(Mg) added to form Magnessium bromide(MgBr-Grignard reagent) with the Bromines. **
 * ** Carbondioxide added to substitued the MgBr (Grignard reagents) **
 * ** The product is further exposed to excess Ammonia (NH3) and heat to form amides at the corresponding positions. **
 * ** The derived product is further exposed to Phosphoruschlorideoxide(POCl3) to convert the amides to nitriles. NBS/heat added Br to the Methyl groups to Methylbromides(CH2-Br). **
 * ** The derived __product(I)__ is put aside for future reaction. **
 * __Starting material (II__): Diphenyl-4-Sulfonic acid Barium salt(C4H20 Ba N2 O6 S2) was reacted with Butyl Lithium ( BuLi) to form a reactive cations.
 * The reactive anaions reacted with 2 moles of Para-ChloroSulfonic acid to form an __intermidiate__ which reacted with POCl3/ DMF to form (__Product II)__
 * Product(I) was added to Product(II) by using Wittig reaction(Ph3-P+) followed be a weak base(KOH) to get the final/ desired product.
 * MACROSCALE AND MICROSCALE ORGANIC EXPERIMENTS. FIFTH EDITION. (PG.88-104).BOSTON, MA : HOUGHTON MIFFLIN COMPANY
 * ORGANIC CHEMISTRY. L.G. WADE,JR. SEVENTH EDITION.
 * PEARSON LEARNING SOLUTIONS. (2010). CATALYST. BOSTON, MA 02116: PEARSON EDUCATION COMPANY.
 * WILLIAMSON,K.MINARD, R.D & MASTERS, K.M. (2007). DISTILLATION.