Category: 3268-21-1

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 3268-21-1 name is 1,4-Diiodo-2,3,5,6-tetramethylbenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 3268-21-1

The Suzuki coupling reaction of 4-bromo-2-phenylpyridine (I) with N-Boc-2-pyrroleboronic acid, using Pd(OAc)2 as the catalyst, was carried out in a glove box due to the air sensitivity of PtBu3, and afforded 4-bromo-2-(N-Boc-pyrrol-2-yl)pyridine (6) with good selectivity. This allowed the remaining Ar-Br bond to be utilised and converted into a boronic ester functional group (7) and mono-Suzuki coupled to 1,4-diiododurene to yield compound (8). The cross-linking group was attached to compound (8) via Suzuki coupling reaction with (4-(non-8-en-1-yloxy)phenyl)boronic acid to yield compound (9). Boc deprotection to give (10) and subsequent cyclometalation using lrCl3.3H20 in 2-ethoxyethanol/H20 at 110 C afforded DIM ER-2 that was converted to the cross-linkable bis-heteroleptic acac phosphor Ir(4- durph-2-pyrpy)2(acac) using acetylacetone and sodium carbonate in 2-ethoxyethanol at 9000.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,4-Diiodo-2,3,5,6-tetramethylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; LOMOX LIMITED; JUDD, Luke; ALDRED, Matthew; KOCH, Gene C.; (71 pag.)WO2018/162880; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common compound: 3268-21-1, name is 1,4-Diiodo-2,3,5,6-tetramethylbenzene, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 3268-21-1

Figure 15 illustrates synthesis of tetracarboxylate ligand 4 in accordance with one embodiment. The synthesis of (3) shown in Figure 15 includes, in one embodiment, combining 1,4-diiodo-2,3,5,6-tetramethylbenzene (shown as (1) in Figure 15 and can be purchased from VWR) (0.60 g, 1.55 mmol) and 3,5-Bis(methoxycarbonyl) phenylboronic acid pinacol ester (shown as (2) in Figure 15 and prepared following Chen et al., A new multidentate hexacarboxylic acid for the construction of porous metal-organic frameworks of diverse structures and porosities, Cryst. Growth Des. 10, 2775-2779 (2010) (1.09 g, 3.41 mmol), K3PO4(1.97 g, 9.30 mmol) and dioxane (15 ml) in 10-20 ml capacity microwave vials and degassed for 10 min with nitrogen. Pd(PPh3)4(0.040 g, 0.03 mmol) was added and the vial was microwave heated with stirring at 150C for 6 hours. After cooling, CH2CI2(30 mL) was added and the organic layer was washed with water (20 raLchi3). The organic layer was dried over MgS04and evaporated under vacuum. The resulting solid was washed with MeOH and then dried under vacuum to give a white solid (0.S6 g, 70%). NMR (S00 MHz, CDCI3): 5 8.73 (t,J= 1.5Hz 2H), 8.10 (d, J = I.6Hz, 4H), 3.99 (s, 12H), 1.94 (s, 12H); 13C NMR (125MHz, CDCI3) delta 166.4, 143.4, 139.8, 134.8, 132.0, 130.9, 129.1, 52.5, 18.2.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3268-21-1, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NORTHWESTERN UNIVERSITY; WILMER, Christopher, E.; LEAF, Michael; SNURR, Randall, Q.; FARHA, Omar, K.; HUPP, Joseph, T.; WO2013/58844; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 3268-21-1 as follows. 3268-21-1

A 200 mL four-neck flask equipped with a stirrer was charged with zinc chloride (7.00 g, 51.4 mmol) and tetrahydrofuran (70 mL) under nitrogen atmosphere, and with stirring, 1,1,1,2-tetrafluoroethane (7.70 g, 75.5 mmol) was blown thereinto at -20 C. Next, a tetrahydrofuran-n-hexane solution of lithium diisopropylamide (1.1 M, 99 mL, 108.5 mmol) was gradually added thereto with the dropping port dipped in the liquid content, and the mixture was stirred at room temperature for 30 minutes. Subsequently, 1,4-diiodo-2,3,5,6-tetramethylbenzene (5.41 g, 14.0 mmol) and tetrakis(triphenylphosphine)palladium (0.65 g, 0.6 mmol) were introduced thereinto and the mixture was stirred at 50 C. for 48 hours. After cooling, an aqueous hydrochloric acid solution was added thereto and the organic layer was washed with 20% saline (50 mL*3 times). The resulting organic layer was dried over anhydrous magnesium sulfate and then the filtrate was concentrated under reduced pressure. The concentrate obtained was purified by silica gel chromatography to give 3.18 g of white solid 1,4-bis(trifluorovinyl)-2,3,5,6-tetramethylbenzene (purity=95.7 wt %, isolated yield=74%). (Results of Analysis) 1H-NMR (Acetone-d6, 400 MHz); 2.18 ppm (d, 12H, Me). 19F-NMR (Acetone-d6, 376 MHz); -158.9 ppm (dd, 2F), -118.3 ppm (ddd, 2F), -104.8 ppm (ddd, 2F). m.p. 91-94 C. GC-MS (m/z):294 (m, 60), 279 (15), 259 (5), 243 (100), 228 (9), 177 (15), 159 (9), 133 (6), 51 (8).

According to the analysis of related databases, 3268-21-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TOSOH FINECHEM CORPORATION; MIYAUCHI, Hideki; KONDO, Norihisa; NAGASAKI, Noritaka; US2020/17429; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com