Category: 4210-32-6

Some common heterocyclic compound, 4210-32-6, name is 4-(tert-Butyl)benzonitrile, molecular formula is C11H13N, 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-(tert-Butyl)benzonitrile

General procedure: To a solution of adiponitrile (219 muL, 1.95 mmol) and the appropriate mononitrile (1.30 mmol) in p-xylene (1 mL) in a carousel tube was added t-BuOK (29.2 mg, 0.26 mmol) in one portion. The reaction vessel was heated in a carousel to 120 °C for 4 h. After cooling to room temperature, CH2Cl2 (ca. 30 mL) was used to transfer the mixture onto a silica cartridge for purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4210-32-6, its application will become more common.

Electric Literature of 4210-32-6, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 4210-32-6, name is 4-(tert-Butyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

BuLi (2.5 M in hexanes, 0.46 mL, 1.14 mmol) wasadded to dry Pri2NH(127.5 mg, 1.3 mmol) in dry THF (2.0 mL) at -78¡ãCand the mixture was stirred at -78¡ãC for 10 min. Compound 41 (200 mg, 1.1 mmol) in dry THF (2.0 mL) was added and the mixturewas stirred for 1 h at -78¡ãC. 4-(1,1-Dimethylethyl)benzonitrile (180 mg, 1.1mmol) in dry THF (2.0 mL) was added and the mixture was stirred for 1 h at-78¡ãC, then at 20¡ãC for 16 h. Water (1.0 mL) was added. The mixturewas diluted with CH2Cl2, washed thrice with brine anddried. Evaporation and washing (EtOH) gave 13c (96.5 mg, 29percent) as a whitesolid: mp 204-206¡ãC; IR nmax3295, 1642 cm-1; 1H NMR ((CD3)2SO)(COSY) d 1.33 (9 H, s, CMe3),2.55 (3 H, s, 5-Me), 6.82 (1 H, s, 4-H), 7.35 (1 H, t, J = 7.6 Hz, 7-H), 7.51 (2 H, d, J= 7.6 Hz, Ph 3,5-H2), 7.54 (1 H, d, J = 7.2 Hz, 6-H), 7.75 (2 H, d, J= 7.6 Hz, Ph 2,6-H2), 8.06 (1 H, d, J = 8.0 Hz, 8-H), 11.48 (1 H, br, NH); 13C NMR((CD3)2SO) (HSQC / HMBC) d 18.75 (Me), 30.97 (CMe3), 34.44 (CMe3),99.60 (4-C), 124.56 (8-C), 124.86 (8a-C), 125.51 (Ph 3,5-C2), 125.72(7-C), 126.56 (Ph 2,6-C2), 131.44 (Ph 1-C), 133.15 (6-C), 133.60(4a-C), 136.69 (5-C), 139.84 (3-C), 151.87 (Ph 4-C), 162.97 (1-C); MS m/z 292.1686 (M + H)+ (C20H22NOrequires 292.1703).

The chemical industry reduces the impact on the environment during synthesis 4-(tert-Butyl)benzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Paine, Helen A.; Nathubhai, Amit; Woon, Esther C.Y.; Sunderland, Peter T.; Wood, Pauline J.; Mahon, Mary F.; Lloyd, Matthew D.; Thompson, Andrew S.; Haikarainen, Teemu; Narwal, Mohit; Lehtioe, Lari; Threadgill, Michael D.; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5891 – 5908;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 4210-32-6, name is 4-(tert-Butyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C11H13N

Step 2: Preparation of 3-(4-(tert-butyl)-phenyl)-6-methoxyisoquinolin-1(2H)-one To a stirred solution of N,N-diethyl-4-methoxy-2-methylbenzamide (1 g, 4.52 mmol) in THF (10 ml) was added n-BuLi (2.82 ml, 4.52 mmol, in hexane) at -78¡ã C. and stirred for 1 h. Then to this 4-(tert-butyl)benzonitrile (0.72 g, 4.52 mmol) was added at same temperature and allowed to warm to room temperature and continued the stirring for another 1 h at room temperature. The reaction mixture was quenched with saturated NH4Cl solution and extracted with EtOac (2*100 ml). The organic phase was washed with brine, dried on Na2SO4, and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (20percent ethyl acetate in pet ether) to get desired compound (0.72 g, 46.7percent) as a solid. 1H NMR (400 MHz, DMSO-d6): delta ppm 11.26(s, 1H), 8.11-8.09 (d, J=8 Hz, 1H), 7.73-7.71 (d, J=8 Hz, 2H), 7.52-7.50 (d, J=8 Hz, 2H), 7.06 (s, 1H), 7.05-7.03 (d, J=8 Hz, 1H), 6.82 (s, 1H), 3.89 (s, 3H), 1.32 (s, 9H); MS: MS m/z 308.2 (M++1).

According to the analysis of related databases, 4210-32-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael; US2013/115190; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 4210-32-6 as follows. HPLC of Formula: C11H13N

3-(4-(1,1-Dimethylethyl)phenyl)-5-methylisoquinolin-1-one (99h). Butyllithium (2.5 M in hexanes, 0.46 mL, 1.14 mmol) was added to dry diisopropylamine (127.5 mg, 1.3 mmol) in dry tetrahydrofuran (2.0 mL) at -78¡ãC and the mixture was stirred at -78¡ãC for 10 min. 2,3,N,N-Tetramethylbenzamide 16 (200 mg, 1.1 mmol) in dry tetrahydrofuran (2.0 mL) was added and the mixture was stirred for 1 h at -78¡ãC. 4-(1 ,1-Dimethylethyl)- benzonitrile (available from Sigma-Aldrich – catalogue number 527785) (180 mg, 1.1 mmol) in dry tetrahydrofuran (2.0 mL) was added and the mixture was stirred for 1 h at -78¡ãC, then at 20¡ãC for 16 h. Water (1.0 mL) was added. The mixture was diluted with dichloromethane. This mixture was washed thrice with brine and dried. The solvent was evaporated and the residue was washed (EtOH) to give 3-(4-(1 ,1-dimethylethyl)- phenyl)-5-methylisoquinolin-1-one 99h (96.5 mg, 29percent) as a white solid: mp 204-206¡ãC; IR vmax3295, 1642 cm”1; 1H NMR ((CD3)2SO) (COSY) delta 1.33 (9 H, s, CMe3), 2.55 (3 H, s, 5-Me), 6.82 (1 H, s, 4-H), 7.35 (1 H, t, J = 7.6 Hz, 7-H), 7.51 (2 H, d, J = 7.6 Hz, Ph 3,5-H2), 7.54 (1 H, d, J = 7.2 Hz, 6-H), 7.75 (2 H, d, J = 7.6 Hz, Ph 2,6-H2), 8.06 (1 H, d, J = 8.0 Hz, 8-H), 1 1.48 (1 H, br, NH); 13C NMR ((CD3)2SO) (HSQC / HMBC) delta 18.75 (Me), 30.97 (CMe3), 34.44 (CMe3), 99.60 (4-C), 124.56 (8-C), 124.86 (8a-C), 125.51 (Ph 3,5-C2), 125.72 (7-C), 126.56 (Ph 2,6-C2), 131.44 (Ph 1-C), 133.15 (6-C), 133.60 (4a-C), 136.69 (5-C), 139.84 (3-C), 151.87 (Ph 4-C), 162.97 (1-C); MS m/z 292.1686 (M + H)+ (C20H22NO requires 292.1703).

According to the analysis of related databases, 4210-32-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF BATH; THREADGILL, Michael David; LLOYD, Matthew David; THOMPSON, Andrew Spencer; NATHUBHAI, Amit; WOOD, Pauline Joy; PAINE, Helen Angharad; KUMPAN, Ekaterina; SUNDERLAND, Peter Thomas; CHUE YEN WOON, Esther; WO2014/87165; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts