Category: 2042-37-7

Some common heterocyclic compound, 2042-37-7, name is 2-Bromobenzonitrile, molecular formula is C7H4BrN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 2042-37-7

EXAMPLE 1 3′-(Imidazo[1,2-alpha]-pyrazin-3-yl)biphenyl-2-carbonitrile A mixture of 2-bromobenzonitrile (9.1 g, 50 mmol), 3-aminobenzeneboronic acid monohydrate (11.6 g, 75 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.73 g, 1.5 mmol) in dimethoxyethane (50 ml) and 2M sodium carbonate solution (25 ml) was heated at 80 C. for 20 h. After cooling to ambient temperature the reaction was partitioned between ethyl acetate (400 ml) and water (400 ml). The organics were washed with brine (400 ml), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel, eluding with isohexane on a gradient of ethyl acetate (0-25%) gave 3′-aminobiphenyl-2-carbonitrile as a colourless oil that solidified on standing to afford a white solid (9.5 g, 98%): deltaH (400 MHz, CDCl3) 3.79 (2H, br), 6.75 (1H, ddd, J 8, 3 and 1), 6.84 (1H, dd, J 3 and 3), 6.92 (1H, dd, J 8 and 3), 7.25 (1H, dd, J 8 and 8), 7.40 (1H, ddd, J 8, 8 and 1), 7.50 (1H, dd, J 8 and 1), 7.62 (1H, ddd, J 8, 8 and 1), 7.73 (1H, dd, J 8 and 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2042-37-7, its application will become more common.

Reference:
Patent; Goodacre, Simon Charles; Hallett, David James; Street, Leslie Joseph; US2004/19057; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 2042-37-7 name is 2-Bromobenzonitrile, 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. 2042-37-7

General procedure: The tetrazole compounds were prepared by a modified literature reported protocol.3 Thus, the aromatic nitrile (1.0 equiv), TBAF.3H2O (0.5 equiv) and TMS-N3 (1.5 equiv) were taken in a screw capped vial equipped with a magnetic stirrer and the resulting mixture was stirred vigorously at 85 oC. The reaction mixture was then transferred to a seperatory funnel and TBAF was removed by washing the organic phase with 1M aqueous HCl solution (20 ml). The organic phase was separated, washed with brine (20 ml) and dried over Na2SO4 and then concentrated in a rotary evaporator. The products were then purified by silica-gel (60-120 mesh) column chromatography or for some cases by recystallisation. Compound 2L was used as a crude mixture for further reaction. The compounds were then characterized by IR, NMR spectroscopy and mass spectrometry. Compounds 2A-B and 2H are reported compounds3 whereas 2C- 2G and 2I- 2L are new.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Bag, Subhendu Sekhar; Talukdar, Sangita; Anjali; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2044 – 2050;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

2042-37-7, Adding some certain compound to certain chemical reactions, such as: 2042-37-7, name is 2-Bromobenzonitrile, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 2042-37-7.

K3PO4 (212 mg, 1 mmol),aryl halides (0.5mmol) and phenylboronicacid (0.75 mmol) were added successively into a dried Schlenk tubewith a magnetic bar under nitrogen. Then a N,N-dimethylacetamide (DMA 0.05 mL) solution of tetraphosphine TPPDA (0.0005 mmol) andPdCl2 (0.0005 mmol), which was reacted at 100 C for 1 h prior to use,was added into the mixture. Afterwards, o-xylene (3 ml) was addedwith syringe. After being stirred for the required time in the preset con-ditions, the reaction mixture was cooled to room temperature. The mix-ture solution was extracted with ethyl acetate (3 5 mL). Combinedorganic phase was washed with brine (3 5 mL) and dried over anhy-drous MgSO4. The dried solution was ltered and puried by silica gelchromatography (petroleum ether 60-90 C) to give a correspondingproduct. Reaction condition: aryl halides 0.5 mmol, phenylboronic acid 0.75 mmol, K3PO4 1.0mmol, o-xylene 3 mL, catalyst PdCl2/TPPDA = 1/1, 90 C, under nitrogen, GC yields.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2042-37-7.

Reference:
Article; Guo, Fei-Chen; Zhou, Rong; Jiang, Zhi-Jie; Wang, Wei; Fu, Hai-Yan; Zheng, Xue-Li; Chen, Hua; Li, Rui-Xiang; Catalysis Communications; vol. 66; (2015); p. 87 – 90;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts