Category: 103273-01-4

Electric Literature of 103273-01-4, A common heterocyclic compound, 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, molecular formula is C10H14BrN, 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.

To a mixture of 2-bromo-4- tert-butylaniline (Compound 1-1, 16.8 g, 74 mmol) and CuCN (13.29 g, 148 mmol) in a 250 mL round-bottom flask was added NMP (N-methylpyrrolidone, 100 mL) . The mixture was heated to reflux under nitrogen until TLC analysis showed full conversion of the starting material. The mixture was cooled to room temperature and the solvent was removed under vacuum. To the residue was added aq. NH40H at 0 C. Ethyl acetate was used for extraction (three times) . The combined organic phase was dried over anhydrous MgSC>4, filtered, and evaporated under vacuum. The residue was purified by flash chromatography (ethyl acetate : hexanes = 1:10) to provide the aminobenzonitrile Compound 1-2 as a yellow solid (10.8 g, 84% yield) . 1H NMR (400 MHz, CDC13) delta 7.39- 7.33 (m, 2H) , 6.70 (d, J = 8.4 Hz, 1H) , 4.32 (br, 2H, NH2), 1.25 (s, 9H) ; 13C NMR (100 MHz, CDC13) delta 147.48, 141.15, 131.77, 128.56, 118.22, 115.32, 95.63, 34.02, 31.21. HRMS (ESI-TOF) m/z Calcd for C11H15N2+ [M+H] + 175.1230, found 175.1235.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; YU, Jin-Quan; (107 pag.)WO2016/123361; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, belongs to bromides-buliding-blocks compound, 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 103273-01-4, SDS of cas: 103273-01-4

200 mL three-necked eggplant flask fully dried (condenser, three-way cock, To a magnetic stirring bar) was added 2-methoxyphenylboronic acid (Wako Pure Chemical Industries, Ltd.) (3.19 g, 10.5 mmol), (0.05 mmol) of 2-bromo-4-tert-butylaniline (2.8 g, 10 mmol), palladium acetate (manufactured by Wako Pure Chemical Industries, Ltd.), 2-dicyclohexylphosphino-2′,6-dimethoxybiphenyl (Manufactured by Sigma-Aldrich Japan Co., Ltd.) (0.041 g, 0.1 mmol) 6.9 g (30 mmol) of potassium phosphate monohydrate (manufactured by Wako Pure Chemical Industries, Ltd.) In addition, suspended in 20 mL of toluene (manufactured by Kanto Chemical Co., Ltd.) The reaction was carried out at 100 C. for 3 hours. To this reaction solution was added 50 mL of water, After extraction with toluene, the organic layer was dried with MgSO 4 (manufactured by Kanto Kagaku Co., Ltd.) The solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent; hexane (Manufactured by KANTO CHEMICAL CO., LTD.) / Ethyl acetate (manufactured by KANTO CHEMICAL CO., LTD.) = 9/1) to obtain 2.40 g (94%, light yellow liquid) of Compound

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, 2-Bromo-4-(tert-butyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mitsui Chemicals Co., Ltd.; Kinoshita, Shinsuke; Kawamura, Kazumori; Ishii, Seiichi; Tanaka, Kenichi; Hanada, shiori; Saito, Yasunori; Hara, Retsu; Mizobuchi, Yusuke; Muroto, Toshihiro; (55 pag.)JP5769443; (2015); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 103273-01-4,Some common heterocyclic compound, 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, molecular formula is C10H14BrN, 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.

2 – Bromo -4 -tert-butylaniline (2 – Bromo – 4 – tertbutylaniline) 40.0g (175.34 mmol), 4 – bromobenzoyl chloride (4 – Bromobenzoyl chloride) 38.4g (175.34 mmol) and THF 360 ml 3 hoursAfter completion of the reaction, the solvent was distilled under reduced pressure. A yellowish solid compound (intermediate (7)) 55.8g (=unitz ) was obtained by solid formation using diisopropyl ether (IPE) to give a solid compound having a yellowish 77.4% color.

The synthetic route of 103273-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Co., Ltd. Leputuo; Wu Weizhen; Han Jiazhong; Jin Huizhen; Jin Xiane; Jin Kuili; Ren Zhezhu; Xi Wenji; Gao Bingzhu; (46 pag.)CN109988119; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 103273-01-4, 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 103273-01-4 as follows.

45.0 g (197.26 mol) of Intermediate 21, 33.7 g (197.26 mol) of 2-methoxybenzoyl chloride and 650 mL of THF were added and the mixture was stirred at room temperature for 3 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. And solidified with diisopropyl ether (IPE) to obtain 63.8 g (yield: 89.3%) of a white solid compound (intermediate (22)).

According to the analysis of related databases, 103273-01-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Samsung Display Co., Ltd.; Raepto Co., Ltd.; Cho Hwan-hui; Bae Seong-su; Oh Yu-jin; Kim Gyu-ri; Jeong Hye-in; Han Gap-jong; Kim Nam-ho; Kim Hye-jeong; (64 pag.)KR2019/25788; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 103273-01-4

2-Bromo-4-tert-butyl-phenylamine (162 g, 0.71 mol) was added dropwise to H2SO4 (410 mL) at room temperature to yield a clear solution. This clear solution was then cooled down to -5 to -10 0C. A solution of KNO3 (82.5 g, 0.82 mol) in H2SO4 (410 mL) was added dropwise while the temperature was maintained between -5 to -10 0C. Upon completion, the reaction mixture was poured into ice / water and extracted with EtOAc. The combined organic layers were washed with 5% Na2CO3 and brine, dried over Na2SO4 and concentrated. The residue was purified by a column chromatography (EtOAc / petroleum ether 1 / 10) to give 2- bromo-4-ter£-butyl-5-nitro-phenylamine as a yellow solid (152 g).

According to the analysis of related databases, 103273-01-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/36412; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 103273-01-4, The chemical industry reduces the impact on the environment during synthesis 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, I believe this compound will play a more active role in future production and life.

General procedure: A solution of 2-bromo-4-isopropylaniline 25a (36 g, 170 mmol) andN-benzyl-4-piperidone (31 mL, 170 mmol) in AcOH (130 mL) wastreated with TMSCN (22 mL, 180 mmol) at room temperature for 5 h.The reaction mixture was neutralized by 8 N aqueous NaOH (380 mL)at 0 C, and the mixture was extracted with AcOEt (500 mL). The organicphase was washed with saturated aqueous NaCl, dried (Na2SO4),filtered, and concentrated in vacuo. The residue was purified by silicagel column chromatography (AcOEt/hexane; 10:90 to 40:60) to affordcompound 26a (55 g, 79%) as a yellow solid.

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, 2-Bromo-4-(tert-butyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Arai, Yoshikazu; Katayama, Katsushi; Koda, Shuichi; Masumura, Makoto; Murata, Kenji; Muto, Tsuyoshi; Nagata, Tsutomu; Okada, Hiroyuki; Saito, Shoichi; Takashima, Kouhei; Yoshida, Ayako; Bioorganic and medicinal chemistry; vol. 28; 6; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 103273-01-4, A common heterocyclic compound, 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, molecular formula is C10H14BrN, 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.

To a suspension of 4-trifluoromethylbenzoic acid (420 mg, 2.2 mmol) in dichloromethane (5 mL) was added N,N-dimethylformamide (1 drop) followed by oxalyl chloride (225 muL, 2.6 mmol) at 0 C. The mixture was warmed to room temperature and stirred for 4 hours before the volatile components were removed under a stream of nitrogen. The crude acid chloride was taken up in dichloromethane (2 mL) and added to a cooled solution of the aniline 39 (500 mg, 2.2 mmol) in dichloromethane (10 mL) and the mixture was stirred for 16 hours at room temperature. The reaction mixture was diluted with dichloromethane (20 mL), washed with saturated aqueous sodium hydrogen carbonate solution (2 x 20 mL) and saturated aqueous ammonium chloride solution (2 x 20 mL), dried over anhydrous magnesium sulfate and concentrated. The crude solid was purified by flash column chromatography using ethyl acetate, hexane (1:49 to 1:24) as an eluent and recrystallisation from isopropyl alcohol, water to obtain the title compound (660 mg, 75%) as a white solid, mp: 151.7-152.7 C; Rf: 0.63 (1:9 ethyl acetate, hexane); IR (vmax (film)): 3343, 2966, 1660, 1509, 1318, 1111, 1065 cm-1; 1H NMR (300 MHz, CDCl3): delta 1.31 (9H, s), 7.41 (1H, s), 7.79 (2H, d, J = 8.0 Hz), 8.04 (2H, d, J = 8.0 Hz), 8.31-8.45 (2H, m) ppm; 13C NMR (75 MHz, CDCl3): delta 31.4, 34.8, 114.1, 121.7, 123.6 (q, J = 270.0 Hz), 125.8, 126.2 (q, J = 3.6 Hz), 127.7, 129.4, 132.9, 133.2 (q, J = 31.2 Hz), 138.1, 149.6, 164.0 ppm; 19F NMR (282 MHz, CDCl3): delta -63.0 ppm; LRMS (+ESI) m/z: 422.0/424.0 ([M+Na]+ 100%); HRMS (ESI)+ Cald for C18H17BrF3NO [M+Na]+: 422.03378/424.03174, found 422.03396/424.03190.

The synthetic route of 103273-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moir, Michael; Boyd, Rochelle; Gunosewoyo, Hendra; Montgomery, Andrew P.; Connor, Mark; Kassiou, Michael; Tetrahedron Letters; vol. 60; 36; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

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 103273-01-4 as follows. Formula: C10H14BrN

General procedure: A Schlenk tube containing Pd(OAc)2 (24.3 mg, 0.108 mmol), K2CO3 (759mg, 5.49 mmol), tricyclohexylphosphine (61.7 mg, 0.220 mmol), anddiphenylacetylene (470 mg, 2.58 mmol) was flushed with N2. NMP (21mL) and 2-bromo-5-tert-butylaniline (525 mg, 2.30 mmol) was added andthe resulting mixture was heated to 110 C. After stirred for 18 h, themixture was cooled to room temperature and then filtered through a shortpad of Celite with EtOAc. The eluent was washed with water and brine,dried over anhydrous Na2SO4, and evaporated to dryness. Purification bysilica-gel column chromatography (hexane/EtOAc as an eluent) afforded1a (460 mg, 1.42 mmol) in 62% yield.

According to the analysis of related databases, 103273-01-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shigeno, Ami; Matsuno, Takashi; Hiroto, Satoru; Shinokubo, Hiroshi; Chemistry Letters; vol. 44; 12; (2015); p. 1703 – 1705;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

To a 500-mL 3-necked round-bottom flask,was placed a solution of 2-bromo-4-tert-butylaniline (1.38 g,6.05 mmol) in dioxane/water(120 mL) then Pd(OAc)2 (135 mg,0.60 mmol),2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.41g,9.15 mmol),PCy3.HBF4 (440 mg,1.19 mmol),and K3P04 (3.81 g,17.97 mmol) were added under nitrogen. The reaction was stirred for 12 h at 110C,quenched by the addition of water,and extracted with EtOAc. The organic extracts were combined and concentrated underreduced pressure. The residue was purified by column chromatography eluting withEtOAc/petroleum ether (1:80) affording 436mg (41%) of the title compound as a colorless oil.Mass Spectrum (LCMS,ESI pos): Calcd. for C12H18N: 176.1 (M+H); Found: 176.1.

The synthetic route of 103273-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; MUNOZ, Benito; BASTOS, Cecilia, M.; PARKS, Daniel; KOMBO, David; (301 pag.)WO2017/62581; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 103273-01-4, These common heterocyclic compound, 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, 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.

General procedure: A mixture of 2-bromo-4-tert-butylaniline (2.28 g, 10 mmol), 2,5-dimethoxytetrahydrofuran (4.2 g, 30 mmol) and glacial acetic acid (150 mL) in a 250 mL three-necked RB flask was refluxed under nitrogen for 17 h. Then it was cooled, poured into aq. HCl (200 mL) and extracted with CH2Cl2, then combined organic phase was washed with water and dried over MgSO4. After workup, the crude product was purified by column chromatography (PE) to afford 3ac as a white powder (1.97 g, 52 %); Rf = 0.28 (PE); m. p. 138 -140 C; 1H-NMR (CDCl3, 300 MHz) delta: 8.18 (d, J = 7.5 Hz, 2H), 7.85 (d, J = 11.4 Hz, 1H), 7.55 (d, J = 10.8 Hz, 1H), 7.42 (m, 3H), 7.29 (m, 2H), 7.12 (d, J = 7.8 Hz, 2H), 1.45 (s, 9H); 13C-NMR (CDCl3, 100 MHz) delta: 153.85, 141.01, 133.88, 131.20, 130.45, 126.03, 125.89, 123.42, 123.20, 120.35, 119.89, 110.18, 36.06, 31.32.

The synthetic route of 103273-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lv, Jun; Liu, Qiancai; Tang, Jie; Perdih, Franc; Kranjc, Kristof; Tetrahedron Letters; vol. 53; 39; (2012); p. 5248 – 5252;,
Bromide – Wikipedia,
bromide – Wiktionary