Month: July 2021

Electric Literature of 583-70-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 583-70-0, name is 2,4-Dimethylbromobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Examples 42-45 Bis-(2,4-dimethylphenyl)chlorophosphine (B42): A solution of 2.92 ml (2161 mmol) of 4-bromo-1,3-dimethylbenzene in 3 ml of Et2O were added at 0 C. to a suspension of 0.5 g (20.56 mmol) of magnesium turnings in 7 ml of THF and 7 ml of Et2O and also a crystal of iodine. The mixture was heated to room temperature, stirred further overnight and slowly added dropwise at 0 C. to a solution of 1.5 ml (10.31 mmol) of Et2NPCl2 in 8 ml of THF. The mixture was heated to room temperature and the solvent was subsequently removed under reduced pressure. After adding 60 ml of hexane, the mixture was filtered through Celite under argon and admixed with hydrogen chloride for 1 hour. After degassing, the resulting solids were filtered off under argon and dried. Yield: 1.4 g (58.3% of theory). 1H NMR (400 MHz, CDCl3) delta, 7.40 (d, Jmeta=4.5 Hz, 2H, arom.), 7.2 (m, 4H, arom.), 2.5 (d, JPH=2.0 Hz, 6H, CH3), 2.4 (s, 6H, CH3). 31P NMR (161.974 MHz, CDCl3) delta, 75.6.

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, 2,4-Dimethylbromobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Meseguer, Benjamin; Militzer, Hans-Christian; Castillon, Sergio; Claver, Carmen; Diaz, Yolanda; Aghmiz, Mohamed; Guiu, Ester; Aghmiz, Ali; Masdeu, Anna; US2005/80047; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 553-94-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 553-94-6, name is 2,5-Dimethylbromobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In a 250mL dry four-neck flask, evacuate and replace the system three times with nitrogen, and then add 60mL of anhydrous ether, 3.77g of magnesium filings (molecular weight 24.3, 155.20mmol, 1.2eq) and a small iodine (15mg) under nitrogen protection. ), Raise the temperature to 60 C, and slowly add about one-fifth of a solution of 2,5-dimethylbromobenzyl ether [25.75g of 2,5-dimethylbromobenzyl (molecular weight 199.09, 129.33mmol) , 1eq) dissolved in 30mL of ether], the temperature did not increase significantly, stirred at this temperature for about 30 minutes, at this time observed the temperature rose significantly, reached a reflux state, at the same time the yellow in the solution faded and turned off-white. The remaining 2,5-dimethylbromobenzyl ether solution was slowly added dropwise, and the drop was completed in about 40 minutes. After dripping and holding for 1 hour, it was observed that the magnesium dust in the reaction solution had basically disappeared. The temperature of the reaction solution was lowered to 0 C, and 46.04 g of ethylene oxide (molecular weight 44.05, 1034.6 mmol, 8.0 eq) was slowly added. After the addition, the temperature was maintained at about 0 C and stirring was continued for 3 hours. 70 mL of saturated ammonium chloride solution was added to extract the reaction. After the tetrahydrofuran was distilled off under negative pressure, the aqueous phase was extracted three times with 40 mL of dichloromethane. The dichloromethane phases were combined and the dichloromethane was evaporated to dryness under negative pressure to obtain 18.87 g (molecular weight 150.22, theoretically obtained). 19.43 g) a white solid. The purity was 97.5%, which was 2,5-dimethylphenylethanol, and the mass yield was 94.69%.

The synthetic route of 2,5-Dimethylbromobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Zhongqi Technology Co., Ltd.; Wu Yaojun; Bu Long; Zhang Pu; Hou Yuanchang; (7 pag.)CN110357774; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 955959-84-9, 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 955959-84-9 as follows.

In a round bottom flask, 4.9 g of aniline, 30 g of starting material X1, t-BuONa 14.5 g, Pd2(dba)3 2.2 g, and (t-Bu)3P 2.3 m were dissolved in 200 ml of toluene, stirred at reflux. The reaction was confirmed by thin layer chromatography (TLC), and after adding water, the reaction was terminated. Use methyl cellulose (MC) to extract organic layers and reduce themAfter pressure filtration, column purification and recrystallization were carried out to obtain 16.2 g (yield 81percent) of IA-1.

According to the analysis of related databases, 955959-84-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dongjin Shimeiken Co., Ltd.; Jin Jintai; Xian Haowan; Jin Dongjun; Lin Donghuan; Li Yingzhen; Lin Dazhe; Han Zhengyou; Pei Weizhen; Jin Yingsen; Li Dongxuan; (49 pag.)CN108689913; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 29086-41-7,Some common heterocyclic compound, 29086-41-7, name is 1,1-Bis(bromomethyl)cyclopropane, molecular formula is C5H8Br2, 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 stirred solution of 1 .78 g (4.80 mmol) of compound 2-1 and 2.2 g (9.7 mmol) of 1 ,1 -bis(bromomethyl)cyclopropane in 20 mL of DMSO was added 3.2 g (9.7 mmol) of CS2CO3. The mixture was stirred at rt for 3 h under argon atmosphere, then diluted with 50 mL of water and extracted with four 100 mL portions of ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous Na2S04. After filtration, the filtrate was concentrated under reduced pressure to afford a residue, which was purified by silica gel column chromatography eluting with 0 to 15 % gradient of EtOAc in PE to afford compound 6-1. LC-MS: m/e = 324 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1-Bis(bromomethyl)cyclopropane, its application will become more common.

Reference:
Patent; ANGEX PHARMACEUTICAL, INC.; WU, Wen-Lian; YANG, Zhiqiang; LEE, Francis; TAN, John Qiang; (112 pag.)WO2019/94143; (2019); 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. 583-75-5, name is 4-Bromo-2-methylaniline, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-2-methylaniline

General procedure: A homogenous mixture of the reagent CTMATB (2 mmol) and substrate 1-9 (2 mmol) were taken in 1:1 ratio in a 50 mL round bottomed flask equipped with reflux condenser in the microwave reactor. 10 mL H2O was added to the mixture and stirred thoroughly. The reaction mixture was placed inside the microwave reactor. The reactor was switched on and kept at a controlled power of P-7 which corresponds to 595 W. Reaction temperature was recorded using the flexible temperature probe attached to the microwave reactor, immediately after the completion of the reaction, and was found to be 90 C. The progress of the reaction was monitored by TLC on silica gel HF254 using ethyl acetate-hexane solvent system (volume ratio varied for different substrates). After completion of the reaction, the product was extracted with 10 mL (2×) ethyl acetate and washed with 5 mL (2×) sodium bicarbonate solution. The crude product thus obtained was subjected to column chromatography over a pad of silica gel using ethyl acetate-hexane solvent system (volume ratio varied for different substrates) to obtain the desired products 1a-9a.

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:
Article; Longkumer, Naruti; Richa, Kikoleho; Karmaker, Rituparna; Kuotsu, Visekhonuo; Supong, Aola; Jamir, Latonglila; Bharali, Pranjal; Sinha, Upasana Bora; Acta Chimica Slovenica; vol. 66; 2; (2019); p. 276 – 283;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 16518-62-0, name is 3-Bromo-N,N-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. Computed Properties of C8H10BrN

It was prepared as outlined in Scheme 1 In an oven-dried 50 mL round bottom flask under an atmosphere of anhydrous argon, THF (10 mL) was added followed by 3-bromo-N,N-dimethylaniline (5.00 mmol, 1.00 g). This clear, colourless solution was cooled to -90 °C using a Juablo cooler with a cold finger and an isopropanol bath in an appropriate sized Dewar. The aniline reagent solution was stirred at this temperature for 15 min to ensure the solution was sufficiently cold. Butyl lithium (3.44 mL, 1.60 M in hexanes) was added dropwise at -90 °C over 20 min. The resulting clear light yellow solution was stirred for 15 min at -90 °C. To this 3-lithium N,N-dimethylaniline intermediate was added N-methoxy-N-methyl-2,2,2-trifluoroacetamide (5.50 mmol, 0.857 g) dissolved in anhydrous THF (4 mL), dropwise over 15 min. The resulting solution was stirred at -90 °C for 30 min then warmed to room temperature by removing the reaction flask from the cooling bath. The resulting reaction mixture was stirred for 16 h at room temperature then extracted with 1 M HCl (3 * 10 mL). The combined aqueous layers were added to a separatory funnel and solid NaHCO3 was added until the solution stopped bubbling. During this addition a yellow liquid formed on the top of the aqueous layer. The aqueous layer was extracted with diethyl ether (3 * 15 mL). The combined organic layers were dried over Na2SO4, gravity filtered and concentrated in vacuo. The crude viscous yellow liquid was purified by flash chromatography on silica gel (5percent ethyl acetate/94percent hexanes/1percent triethylamine, Rf: 0.38) to afford the desired product as a clear yellow liquid (0.854 g, 79percent): 1HNMR (CDCl3): d 3.02 (s, 6H), 7.02?7.05 (m, 1H), 7.36?7.38 (m,3H) (Supplementary Fig. S1). 13C NMR (CDCl3): d 40.0, 112.3,116.8 (q, JC,F = 298.2 Hz), 117.9, 119.1, 129.5, 130.4, 150.5, 181.0(q, JC,F = 34.3 Hz) (Supplementary Fig. S2). IR (Neat): 2898 (m),2814 (w), 1709 (s), 1600 (s), 1573 (s), 1503 (s), 1437 (m), 1363(m), 1105 (s), 1007 (s) cm1 (Supplementary Fig. S3). LRMS m/z: 218 (M+1, 11), 217 (M+, 100), 216 (74), 148 (24), 120 (24), 119(13), 118 (10), 104 (10), 77 (11), 74 (13) (Supplementary Fig. S4). HRMS (ESI): MH+ found 218.0786, calculated for C10H11F3-NO+ = 218.0787(Supplementary Fig. S5). HPLC: retention time 2.59 min; purity 96.1percent (Supplementary Fig. S6).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16518-62-0, its application will become more common.

Reference:
Article; Jollymore-Hughes, Courtney T.; Pottie, Ian R.; Martin, Earl; Rosenberry, Terrone L.; Darvesh, Sultan; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5270 – 5279;,
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. 699-03-6, name is 1-(4-Bromophenyl)-N-methylmethanamine, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-(4-Bromophenyl)-N-methylmethanamine

A mixture of l-(4-bromophenyl)-N-methylmethanamine (14.0 g, 70.0 mmol), 2-(but- 3-yn-l-yl)isoindoline-l,3-dione (16.5 g, 83.0 mmol), Cul (3.33 g, 17.5 mmol) and CS2CO3 (114 g, 351 mmol) in deoxygenated dioxane (280 mL) was further deoxygenated by bubbling nitrogen gas for 1.25 h. through the mixture. PdCl2([l,r-bis(diphenylphosphino)ferrocene]) (5.71 g, 7.00 mmol) was added and the mixture further deoxygenated with nitrogen for 1 h before heating to 80C for 18 h under an atm. of N2. The reaction was allowed to cool to room temperature and filtered through celite with EtOAc. The organic mother liquor was washed with 1 molar NaOH, water, brine, dried with Na2S04, filtered and concentrated in vacuo. The residue was chromatographed on silica gel (330 g Isco column, 1 to 10% MeOH in DCM with 1% N Eh in the eluents over 36 min.) to give 23.3 g of 2-(4-(4- ((methylamino)methyl)phenyl)but-3- yn-l-yl)isoindoline-l,3-dione as a black oil that was 86% 74 by weight. The raw product was used as is in the next reaction. 1H NMR (400MHz, chloroform-d) d = 7.87 (dd, =3.0, 5.5 Hz, 2H), 7.73 (dd, J=3. l, 5.4 Hz, 2H), 7.31 – 7.28 (m, 2H), 7.23 – 7.19 (m, 2H), 3.97 (t, J=1 A Hz, 2H), 2.83 (t, J=1 A Hz, 2H), 2.43 (s, 3H), 1.19 (t, J=12 Hz, 2H). LC/MS RT = 0.49 min., 319.0 [M+H]+

The synthetic route of 699-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ADVITECH ADVISORY AND TECHNOLOGIES SA; BECK, Brent Christopher; PERALES, Joe B.; SPEAKE, Jason D.; FERRANDO, Ilaria; (28 pag.)WO2019/115000; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 2550-36-9, 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. 2550-36-9 name is (Bromomethyl)cyclohexane, 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.

Step 1: To a solution of 3-bromo-6-methylimidazo[1 ,5-a]pyrazin-8(7H)-one (1 g, 4.39 mmol, 1 eq) and Cs2003 (2.86 g, 8.78 mmol, 2 eq) in DMF (20 mL) was added (bromomethyl)cyclohexane (1 .55 g, 8.78 mmol, 1.22 mL, 2 eq). The mixture was stirred at6000 for 18 hour. The reaction mixture was filtered and the filtrate was concentrated. The crude mixture was purified by flash chromatography with petroleum ether:ethyl acetate = 5:1 3:1. 3-bromo-7-(cyclohexylmethyl)-6-methylimidazo[1 ,5-a]pyrazin-8(7H)-one (1 g, 3.02 mmol, 69% yield) was obtained.1H NMR (ODd3, 400 MHz): 7.86 (s, 1H), 6.80 (s, 1H), 3.79 (d, J= 7.2 Hz, 2H), 2.29 (s,3H), 1.75 -1.66 (m, 6H), 1.22 – 1.04 (m, 5H).LC-MS: tR = 0.791 mm (method 15), mlz= 325.9 [M + H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (Bromomethyl)cyclohexane, and friends who are interested can also refer to it.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (159 pag.)WO2016/174188; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 156682-52-9, name is 1,4-Dibromo-2,3-difluorobenzene, molecular formula is C6H2Br2F2, 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. HPLC of Formula: C6H2Br2F2

Preparation of iso-PrMgCl-LiCl-A sample of LiCl (4.56 g, 107.6 mmol) was dried under high vacuum with a heat gun for 10 min. To the dry solid under a N2 atmosphere at 23 C. was added iso-PrMgCl (53.8 mL, 107.6 mmol, 2M solution in THF) and the resulting mixture was stirred at 23 C. for 3 days.To a solution of D-1c (1.29 mL, 10 mmol) in THF (5 mL) at 40 C. was added the iso-PrMgCl-LiCl solution (5.5 mL, 11 mmol, 2.0M in THF) at a rate that maintained the reaction temperature below -30 C. Stirring was continued at -35 to -30 C. for 1 h then warmed to -7 C. for an additional 1 h. The reaction mixture was cooled to -30 C. and DMF (1.00 mL, 13 mmol) was added in one portion (temperature rose to -23 C.) and stirring continued for 3.5 h at -25 to +15 C. The reaction mixture was poured into 1M H2SO4 and ice and the resulting mixture was saturated with solid NaCl and twice extracted with MTBE. The combined extracts were dried (MgSO4), filtered and concentrated in vacuo to afford 2.17 g (98%) of D-1d as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 156682-52-9, its application will become more common.

Reference:
Patent; Roche Palo Alto LLC; US2008/249151; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 39478-78-9, name is 5-Bromo-2-methylaniline, 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 39478-78-9, Computed Properties of C7H8BrN

General procedure: Under N2 atmosphere, a mixture of 6 (100.0 mg, 0.26 mmol),Pd(pph3)4 (30.0 mg, 0.026 mmol), 2.0M aq Na2CO3 (0.29 ml,0.78 mmol) and 1-Methyl-1H-pyrazole-5-boronic acid pinacolester (108.2 mg, 0.52 mmol) in 1,4-Dioxane (0.65 ml) was heated to90 C and stirred for 6 h. The reaction mixture was cooled, dilutedwith ethyl acetate, washed with water, dried over anhydrousNa2SO4, filtered and concentrated under vacuum. Purification onsilica using a solvent gradient of 10-30% ethyl acetate in hexanesyielded the desired compound 1j (77.0 mg, 77.5%). Compounds 1akwere prepared according to general procedure as described forcompound 1j using corresponding aryl bromide 2-4 and theappropriate boronic acid or boronic acid pinacol ester. The characterizationdata for compounds 1a-k were provided below.

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, 5-Bromo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yu, Jiang; Zhang, Lanxi; Yan, Guoyi; Zhou, Peiting; Cao, Chaoguo; Zhou, Fei; Li, Xinghai; Chen, Yuanwei; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 265 – 281;,
Bromide – Wikipedia,
bromide – Wiktionary