Category: 101066-87-9

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 101066-87-9, name is 4-Iodo-2-(trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., Quality Control of 4-Iodo-2-(trifluoromethyl)benzonitrile

To the suspension of zinc powder (without activation, 65.4 mg, 1.0 mmol, Aldrich 99.995 % purity) in DMPU (0.5 mL), trifluoromethyl iodide (ca. 2.5 mmol, sufficiently dissolved in the solution) was added at room temperature under argon atmosphere. The solution was stirred for 2 h, and CuI (9.5 mg, 0.05 mmol, 10 mol %) and 4-iodo-2-(trifluoromethyl)benzonitrile (1c, 148.5 mg, 0.5 mmol) were added. The reaction mixture was stirred at 50 C for 24 h. The reaction mixture was quenched with H2O (5 mL), and then Et2O (5 mL) was added. After filtration over celite, the organic layer was separated, and the aqueous layer was extracted with Et2O (5 mL ¡Á 3). The combined organic layer was washed with brine (10 mL), dried over Na2SO4, and evaporated. The resulting crude product was purified by silica gel column chromatography (pentane/Et2O 9:1) to give the product 2c (83 mg, 70% yield) as a colorless liquid. 1H NMR (300 MHz, CDCl3) delta 8.06 (s, 1H), 8.03 (d, J =8.2 Hz, 1H), 7.98 (d, J = 8.2 Hz, 1H); 13C NMR (400 MHz, CDCl3) delta 135.5, 135.0 (q, JCF = 34.4 Hz), 134.0 (q, JCF = 33.5 Hz), 129.3 (q, JCF = 3.6 Hz), 124.1-123.9 (m), 122.3 (q, JCF =271.9 Hz), 121.6 (q, JCF = 272.7 Hz), 114.1, 113.9; 19F NMR (282 MHz, CDCl3) delta -62.2 (s, 3F), -63.6 (s, 3F); HRMS-ESITOF (m/z): [M – H]- calcd for C9H2F6N, 238.0091; found, 238.0086; FTIR (neat, cm-1) 2238, 1344, 1146, 1279, 1082.

The synthetic route of 101066-87-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nakamura, Yuzo; Fujiu, Motohiro; Murase, Tatsuya; Itoh, Yoshimitsu; Serizawa, Hiroki; Aikawa, Kohsuke; Mikami, Koichi; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 2404 – 2409;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 101066-87-9, name is 4-Iodo-2-(trifluoromethyl)benzonitrile, its 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. Safety of 4-Iodo-2-(trifluoromethyl)benzonitrile

[0443] A suspension of trans-1-(4-methoxybenzyl)hexahydropyrano[3,4-d]imidazol-2(3H)-one [racemic (¡À)] (0.25 g, 0.95 mmol), 4-iodo-2-(trifluoromethyl)benzonitrile (0.28 g, 0.95 mmol), trans-N,N?-dimethylcyclohexane-1,2-diamine (0.032 g, 0.29 mmol) and potassium carbonate (0.395 g, 2.86 mmol) in toluene (15 mL) was degassed for 30 min in a microwave vial. CuI (0.009 g, 0.05 mmol) was added and the vial was sealed with an aluminum cap. The sealed vial was kept in a preheated oil bath at 110 C. and stirred for 12 h. The reaction mixture was cooled to RT, filtered through a pad of celite, and filtrates were concentrated under reduced pressure to give a black residue. The residue was purified by column chromatography on silica gel (dichloromethane/methanol=100:0 to 99:1) to give the title compound (0.17 g, 41.0%) as an off white solid. LCMS: m/z 432.1 [M+H]+; 1H NMR (400 MHz, CDCl3) delta 7.80-7.74 (m, 2H), 7.54 (d, 1H), 7.20 (d, 2H), 6.84 (d, 2H), 4.50 (d, 1H), 4.40-4.30 (m, 2H), 4.15-4.05 (m, 1H), 3.80 (s, 3H), 3.65 (ddd, 1H), 3.50-3.20 (m, 2H), 3.10 (ddd, 1H), 1.90 (d, 1H), 1.72-1.68 (m, 1H).

The synthetic route of 4-Iodo-2-(trifluoromethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bock, Mark Gary; Chikkanna, Dinesh; Gerspacher, Marc; Khairnar, Vinayak; Lagu, Bharat; Pandit, Chetan; US2014/329858; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 101066-87-9, 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 101066-87-9 as follows.

Reference Example 88 4-[(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-ethyl-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile A suspension of (4S,5S)-4-(tert-butyldimethylsilyloxy)-5-ethylpyrrolidin-2-one (6.00 g), 4-iodo-2-trifluoromethylbenzonitrile (8.42 g), cesium carbonate (12.05 g), tris(dibenzylideneacetone)dipalladium(0) (1.13 g) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (2.14 g) in toluene (70 mL) was stirred at 80 C. for 18 hr. Water and ethyl acetate were added to the reaction mixture and insuluble material was filtered off. The filtrate was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1?1/2) to give the title compound as a pale-yellow solid (yield: 7.76 g, 76%). 1H-NMR(CDCl3)delta:0.14(3H,s), 0.14(3H,s), 0.93(9H,s), 0.96(3H,t,J=7.5 Hz), 1.60-1.78(1H,m), 1.77-1.94(1H,m), 2.66(1H,dd,J=17.0,6.8 Hz), 2.76(1H,dd,J=17.0,7.2 Hz), 4.16-4.26(1H,m), 4.66(1H,q,J=6.9 Hz), 7.81-7.87(2H,m), 7.94-7.99(1H,m).

According to the analysis of related databases, 101066-87-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2009/42967; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com