Tag: M.W=200-300

Application of 30273-40-6,Some common heterocyclic compound, 30273-40-6, name is 4-Bromo-2,5-dimethylaniline, molecular formula is C8H10BrN, 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.

Preparation example 1 – Process (a) – compound (Na) to compound (VII) : 4′-tert-butyl-2,5- diotamethylbiotaphenyl-4-amiotane – intermediate (VII-P; The reaction is carried out using inert conditions (argon or nitrogen atmosphere, dry solvents). A suspension of 6.4 g (36.0 mmol) of (4-tert-butylphenyl)boroniotac acid, 6.0 g (30.0 mmol) of 4- bromo-2,5-diotamethylaniotaliotane, 29.3 g (90 mmol) caesium carbonate and 0.7 g (0.6 mmol) tetrakiotas(triotaphenylphosphiotan)palladiotaum in 75 ml of 1 ,2-diotamethoxyethan was stirred for 16 hrs at8O0C. At room temperature 25 ml of water and 75 ml of toluene were added. The organic layer was separated, the watery layer was again extracted using 75 ml of toluene. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. Column chromatographie (cyclohexane / ethylacetate : 2/1 ) yielded 5.5g (21 ,7 mmol) 72 % of 4′-tert- butyl-2,5-diotamethylbiotaphenyl-4-amiotane (log P (pH 2.3) = 3.65.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2,5-dimethylaniline, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AG; WO2007/31512; (2007); A2;,
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. 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H2BrF3

2L three-necked flask, nitrogen protection, cast diisopropylamine, tetrahydrofuran 750g,Cooling -40 dropping n-butyl lithium, dropping temperature insulation reaction 30min, cooling to -78 , dropping raw materials3,4,5, -trifluorobromobenzene, dropping off,-78 insulation 2h.The temperature was raised to -60 C began dropping dimethyl sulfate,Maintain the temperature is not higher than -30 , the dropping was completed naturally rose to room temperature, incubated for 30min.Stop the reaction, the pump off the pressure of tetrahydrofuran,Add 400g of water,Dichloroethane extraction, the organic phase was washed again, concentrated under reduced pressure distillation, to obtain the final product 2-methyl-3,4,5-trifluorobromobenzene purity of 99.5% or more, a yield of 61%.

According to the analysis of related databases, 138526-69-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bengbu Zhong Shi Chemical Co., Ltd.; Yang Qing; Zhang Hao; Zhao Shimin; Xu Jianxiao; (4 pag.)CN105967974; (2016); 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. 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H2BrF3

In an oven-dried flask, dried halogen-group-containing compounds (2.3 equiv) were added to dry THF containing magnesium metal (Mg) (2.3 equiv, with glass pieces to activate the magnesium metal) at room temperature under nitrogen. The reaction mixture was stirred vigorously until Grignard generation occurred. The lactone (1 equiv dissolved in 40 mL of THF) was added dropwise to the Grignard reagent solution, and the mixture was stirred at room temperature for 16 h and monitored by TLC. The mixture was treated with saturated aqueous NH4Cl (20 mL) and then extracted with AcOEt (3¡Á10mL). The combined organic phases were dried over Na2SO4 and the solvent was removed by an evaporator. The residue was purified by silica-gel column chromatography (AcOEt/hexane). In another experiment, the ring-opening reactions of homoserine lactone with select Grignard reagents were carried out using 2.7 equiv ArMgBr at r.t. and 50C for 2 h.

According to the analysis of related databases, 327-52-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Guendo?du, Oezlem; Turhan, P?nar; Koese, Aytekin; Altunda?, Ramazan; Kara, Yunus; Tetrahedron Asymmetry; vol. 28; 9; (2017); p. 1163 – 1168;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1435-53-6, A common heterocyclic compound, 1435-53-6, name is 2,4-Dibromo-1-fluorobenzene, molecular formula is C6H3Br2F, 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: 8.1 1,3-Diphenyl-4-fluorobenzene (11a): Starting with 10 (100 mg, 0.39 mmol), Cs2CO3 (253 mg, 0.78 mmol), Pd(PPh3)4 (3 mol%), phenylboronic acid (94 mg, 0.78 mmol) and 1,4-dioxane (4 mL), 11a was isolated as a colorless oil (54 mg, 55%). 1H NMR (300 MHz, CDCl3): delta = 7.09-7.16 (m, 1H, ArH), 7.23-7.32 (m, 2H, ArH), 7.33-7.45 (m, 5H, ArH), 7.47-7.63 (m, 5H, ArH). 13C NMR (75 MHz, CDCl3): delta = 116.3 (d, J = 23.6 Hz, CH), 127.1 (2CH), 127.6 (d, J = 8.02 Hz, CH), 128.6 (2CH), 128.9 (2CH), 129.1 (CH), 129.6 (CH), 130.9 (CH), 132.5 (C), 135.8 (C), 137.7 (d, J = 3.57 Hz, C), 140.2 (C), 159.4, (d, JCF = 249.0 Hz, CF). 19F NMR (282 MHz, CDCl3): delta = -120.67 (CF). IR (ATR, cm-1): , 3029 (w), 2956 (w), 2927 (w), 2857 (w), 1948 (w), 1883 (w), 1806 (w), 1723 (m), 1600 (w), 1539 (w), 1478 (s), 1392 (w), 1332 (w), 1257 (m), 1183 (w), 1121 (m), 1073 (m), 1000 (w), 945 (w), 892 (m), 823 (s), 759 (s), 721 (m), 693 (s), 631 (s), 584 (s), 539 (m). MS (EI, 70 eV); m/z (%) = 248 (100) [M]+. HRMS (EI) calcd. for C18H13OF [M]+: 248.09958; found 248.89357.

The synthetic route of 1435-53-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sharif, Muhammad; Maalik, Aneela; Reimann, Sebastian; Feist, Holger; Iqbal, Jamshed; Patonay, Tamas; Villinger, Alexander; Langer, Peter; Journal of Fluorine Chemistry; vol. 146; (2013); p. 19 – 36;,
Bromide – Wikipedia,
bromide – Wiktionary

73918-56-6, name is 2-(4-Bromophenyl)ethanamine, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 2-(4-Bromophenyl)ethanamine

Preparation of N-(4-bromophenethyl)-2,2,2-trifluoroacetamide:; To a solution of 2-(4-bromophenyl)ethanamine (10 g, 50 mmol) and NEt3 (13.9 mL, 100 mmol) in 50 mL of dry THF at room temperature was slowly added TFAA (7.76 mL, 55 mmol). After stirring at room temperature for 1 h, the reaction mixture was quenched with Sat. NaHCO3 solution, extracted with EtOAc, washed with brine, dried over Na2SO4, and evaporated in vaco to give N-(4-bromophenethyl)-2,2,2-trifluoroacetamide as a white solid.

The synthetic route of 73918-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Askew, Benny C.; Aya, Toshihiro; Biswas, Kaustav; Cai, Guolin; Chen, Jian J.; Han, Nianhe; Liu, Qingyian; Nguyen, Thomas; Nishimura, Nobuko; Nomak, Rana; Peterkin, Tanya; Qian, Wenyuan; Yang, Kevin; Yuan, Chester Chenguang; Zhu, Jiawang; D’ Amico, Derin C.; Human, Jason B.; Huang, Qi; US2006/25400; (2006); A1;,
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 40161-54-4 as follows. SDS of cas: 40161-54-4

To a mixture of 1-bromo-2-fluoro-4- (trifluoromethyl) benzene (5.0 g, 0.02 mol) in EtOH (10 mL) was added Pd (dppf) Cl2 (1.46 g, 0.2 mmol ) and AcONa (3.37 g, 0.041 mol) , and the resulting mixture was stirred at 80under an atmosphere of CO (50 psi) for 8 hours. The mixture was then filtrated and the filtrate was partitioned with ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel (eluting with PE:EA10:1) to give the title compound. 1H NMR (400MHz, CDCl3) delta: 8.04-8.08 (t, 1H, J7.6 Hz) , 7.49-7.47 (d, 1H, J8.0 Hz) , 7.43-7.40 (d, 1H, J10.4 Hz) , 4.44-4.40 (q, 2H, J7.2 Hz) , 1.43-1.38 (t, 3H, J7.2Hz) .

According to the analysis of related databases, 40161-54-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BIFTU, Tesfaye; BIJU, Purakkatle; COLLETTI, Steven L.; CUI, Mingxiang; HAGMANN, William K.; HU, Bin; JOSIEN, Hubert; KAR, Nam Fung; NAIR, Anilkumar; NARGUND, Ravi; SPERBECK, Donald M.; ZHU, Chen; WO2015/51725; (2015); A1;,
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. 51554-93-9, name is 1-Bromo-4-octylbenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 51554-93-9

General Procedure W: Synthesis of an alpha-beta unsaturated ketoneAn organometalic reagent (1-3 equivalents, preferably 1.1 equivalents) is added to a solution of a beta-alkoxy enone in an organic solvent (preferably THF) at about -78 C-room temperature (preferably 0 0C). Following the addition the reaction mixture is allowed to warm to about room temperature. After Ih IN HCl is added until a pH of 1 is obtained. The reaction mixture is taken through an aqueous work-up and the crude product can be purified by chromatography.Exemplification of General Procedure W: Preparation of 3-(4-octylphenyl)cyclohex-2-enoneTo a suspension of magnesium (1.477 g, 60.8 mmol) in THF (56 mL) was added 1-bromo- 4-octylbenzene (15.00 g, 55.7 mmol). After stirring for about 6h the reaction mixture was added with filtering to a solution of 3-ethoxycyclohex-2-enone (7.10 g, 50.6 mmol) in THF (28.0 mL) at 0 0C. Following the addition the reaction mixture was allowed to warm to room temperature. After Ih IN HCl was added until a pH of 1 was obtained. The reaction mixture was diluted with Et2O and the organic layer was separated, washed with NaHCO3, and brine, dried with Na2SO4, filtered and concentrated in vacuo. The crude product was purified by chromatography on silica gel (EtOAc/Hep) to provide 3-(4-octylphenyl)cyclohex-2 -enone (9.5 g, 33.4 mmol, 65.9 % yield) as a colorless oil.LCMS (Table 1, Method a) R1 = 4.53 min; m/z: 285 (M-H)-; IH NMR (400 MHz, DMSO- d6) 5 7.57 (d, 2H), 7.25 (d, 2H), 6.34 (s, IH), 2.76 (dd, 2H), 2.60 (dd, 2H), 2.40 (dd, 2H), 2.03 (dddd, 2H), 1.58-1.55 (m, 2H), 1.27-1.24 (m, 10H), 0.85 (t, 3H).

The synthetic route of 51554-93-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2008/79382; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

22034-13-5, name is 4-Bromobenzo[c][1,2,5]thiadiazole, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C6H3BrN2S

To a flask equipped with a reflux device, 2.7 g (24.2 mmol) of t-butoxypotassium, 0.3 g (0.4 mmol) of a Pd catalyst (PEPPSI?-IPr), 70 mL of toluene, 4.3 g (20.2 mmol) of the compound (b), and 1.8 mL (22.2 mmol) of pyrrolidine were added, and it was refluxed at 120¡ã C. for three hours under a nitrogen atmosphere. After a reaction was finished, solids in a reaction solution were removed by filtration, the filtrate was condensed, and then refinement was performed by column chromatography using dichloromethane as a developing solution, to thereby obtain a compound (c2) (2.9 g, 14 mmol, yield: 70percent).

The synthetic route of 22034-13-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGC Inc.; MIYAKE, Noriaki; Okada, Satoshi; Irisawa, Jun; Konishi, Teppei; Matsuura, Keigo; US2018/346729; (2018); A1;,
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. 73790-19-9, name is 5-Bromo-2,2-dimethylbenzo[d][1,3]dioxole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 5-Bromo-2,2-dimethylbenzo[d][1,3]dioxole

PREPARATION 158 2,2-Dimethyl-1,3-benzodioxol-5-ylboronic acid Obtained as a green solid (47%), m.p. 174-176 C., from 5-bromo-2,2-dimethyl-1,3-benzodioxole (GB-A-2187452) and trimethyl borate, using the procedure of Preparation 101. delta(DMSOd6): 1.60 (s,6H), 6.77 (d,1H), 7.17 (s,1H), 7.28 (d,1H), 7.80 (s,2H).

According to the analysis of related databases, 73790-19-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer INC; US6387931; (2002); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 67567-26-4, 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. 67567-26-4 name is 4-Bromo-2,6-difluoroaniline, 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.

A mixture of 4-bromo-2,6-difluoro-aniline (4.16 g, 20.0 mmol, 1.00 eq.) and ethoxycarbothioylsulfanyl potassium (7.69 g, 48.0 mmol, 2.40 eq.) in DMF (25 mL) was stirred at 130C overnight, then cooled to room temperature, diluted with 1 N HCl (150 mL) and stirred at room temperature for 1 h. The resulting solid was filtered and washed with water and dried. The resulting material was suspended in CH2Cl2 (25 mL) and SO2Cl2 (27.5 g, 16.5 mL, 200 mmol, 10.0 eq.) was added slowly and stirred at room temperature for 48 h. Water was added slowly at 0 C to quenched the reaction. The resulting precipitate was collected by filtration and purified over silica with ethyl acetate in hexanes (2 to 10% gradient) to give 6-bromo-2-chloro-4-fluoro- 1,3-benzothiazole (5.08 g, 95.3%). MS m/z 266.1, 268.0, 270.0 [M+H]+.

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

Reference:
Patent; PTC THERAPEUTICS, INC.; ZHANG, Nanjing; BABU, Suresh; BARRAZA, Scott J.; BHATTACHARYYA, Anuradha; CHEN, Guangming; KARP, Gary Mitchell; KASSICK, Andrew J.; MAZZOTTI, Anthony R.; MOON, Young-Choon; NARASIMHAN, Jana; SYDORENKO, Nadiya; TURPOFF, Anthony; WOLL, Matthew, G.; YAN, Wuming; (0 pag.)WO2020/5877; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary