Month: February 2021

These common heterocyclic compound, 314084-61-2, name is 2-Bromo-1,3-diethyl-5-methylbenzene, 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. Formula: C11H15Br

Under a nitrogen atmosphere, 13.9 G of malonic acid dinitrile are added at normal pressure and room temperature to 20.4 g of pulverulent sodium hydroxide in 240 g of 1-methyl-2- pyrrolidone. After the addition of 45.5 g of 2-bromo-1, 3-diethyl-5-methylbenzene, the reaction mixture is heated to 125C with stirring. At that temperature, a mixture of 1.3 g of triphenylphosphine, 1.06 g of a commercially AVAILABLE PALLADIUM (II) chloride solution in concentrated hydrochloric acid (20% Pd content corresponding to 0.354 g of Pd (LI) chloride and 0.708 g of concentrated hydrochloric acid) and 97.6 g of 1-methyl-2-pyrrolidone is added. Stirring is carried out for a further 3 hours at from 125 to 130C, and 283 g of diluent are distilled off at reduced pressure (from 17 to 100 mbar). After cooling to room temp- erature, the reaction mixture is added to 70 g of water. Following the addition of 38 g of concentrated hydrochloric acid (a pH value of less than 5 is then established), the precipitated solid is filtered off and washed with 60 g of water. After drying, 42.4 G of 2- (2, 6- diethyl-4-methylphenyl) malonic acid dinitrile (content 92.3%, yield 92.3%) having a melting point of from 74 to 78C are obtained.Example P4: Preparation of 2- (2, 6-diethyl-4-methylphenyl) malonic acid dinitrile Under a nitrogen atmosphere and at normal pressure, 14 g (217 MMOL) of malonic acid dinitrile dissolved in 7 ml of 1-methyl-2-pyrrolidone are added dropwise in the course of 30 minutes, at from 20 to 25C, to a mechanically stirred mixture of 24.1 g (600 MMOL) of sodium hydroxide (pellets) in 300 ml of 1-methyl-2-pyrrolidone. Evacuation to from 10 to 30 mbar is carried out and, at from 80 to 100C, 113 g of solvent are distilled off. After establishing normal pressure, 48 g (content 94.9% ; 200 MMOL) of 2-bromo-1, 3-DIETHYL-5- METHYLBENZENE are added and the reaction mixture is heated to 130C. At that temperature, a mixture of 0.26 g (1 MMOL) of triphenylphosphine, 0.21 g of a commercially available palladium (li) chloride solution in concentrated hydrochloric acid (20% Pd content corresponding to 0.071 g (400 UMOL) of PALLADIUM (II) CHLORIDE in 0.142 g of concentrated hydrochloric acid) and 19.5 g of 1-methyl-2-pyrrolidone is added. The reaction mixture is stirred for from 2 to 3 hours at from 125 to 140C, nitrogen being introduced below the surface. A further 165 g of solvent are distilled off at from 20 to 60 mbar. 2.3 g of Hyflo and 150 ml of water are added to the residue which has been cooled to 50C. The reaction mixture is stirred vigorously for 10 minutes and then clarified by filtration over Hyflo. The filter is subsequently washed with 55 ml of water. The combined aqueous phases are extracted once with 91 g of toluene. The organic phase is separated off and discarded. 30 g of toluene/water are distilled off from the aqueous phase at from 20 to 70C and from 200 to 250 mbar. At from 20 to 25C there are added to the distillation sump, in the course of from 60 to 80 minutes, 45.7 g of 32% hydrochloric acid, during the course of which the product crystallises out and the pH value falls to from 4.0 to 4.5. Filtration with suction is carried out, followed by washing with 120 ml of water (divided into 2 portions). The product is dried in a vacuum drying cabinet for 16 hours at from 100 to 250 mbar. 42.2 g (content 98.2% ; yield 97.6%) of 2- (2, 6-DIETHYL-4-METHYLPHENYL) MALONIC acid dinitrile are obtained.

The synthetic route of 2-Bromo-1,3-diethyl-5-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2004/50607; (2004); 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 1647-26-3 as follows. Recommanded Product: 1647-26-3

Into a 250-mE 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed magnesium (420 mg, 17.50 mmol, 1.10 equiv), a solution of (2-bromoethyl)cyclohexane (3 g, 15.71 mmol, 1.00 equiv) in tetrahydroffiran (50 mE). The solutionwas refluxed for 3 hours, then cooled to room temperature. Into another 250-mE 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of trimethyl borate (2.46 g, 23.65 mmol, 1.50 equiv) in tetrahydroffiran (50 mE) with stirring at -78 C. To this mixture was added the above prepared solution. The resulting mixture was stirred for 3 hours at room temperature. To the resulting mixture was then added KHF2 (4.926 g, 63.15 mmol, 4.00 equiv) and water (80 mE). The resulting solution was stirred overnight at room temperature. The solvent was removed under reduced pressure. The residue was washed with 3×100 mE of propan-2-one and the resulting filtrate was then concentrated under vacuum to yield potassium (2-cyclohexylethyl)trifluoroborate as a white solid.

According to the analysis of related databases, 1647-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Gaul, Micheal; Xu, Guozhang; Yang, Shyh-Ming; Lu, Tianbao; Zhang, Rui; Song, Fengbin; (75 pag.)US2018/65934; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 452-74-4, 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. 452-74-4, name is 1-Bromo-2-fluoro-4-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows.

[000891j To a stirred solution of compound 1 (8 g, 1 eq) in Conc. H2S04 (35 mL), nitrating mixture (13.2 mL Conc. HN03 + 5 mL Conc. H2S04) was added at 0 C and stirred at same temperature for 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured onto ice water and basified to pH 9 using 2N NaOH. The precipitated solid was filtered, washed with water and dried under reduced pressure to afford the title compound 2. LCMS (mlz): 235 (M + 1).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-fluoro-4-methylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 615-59-8, The chemical industry reduces the impact on the environment during synthesis 615-59-8, name is 1,4-Dibromo-2-methylbenzene, I believe this compound will play a more active role in future production and life.

2,5-dibromotoluene (10 g, 40 mmol)Was dissolved in anhydrous tetrahydrofuran (40 mL). N-Butyllithium (10 g, 160 mmol) was slowly dropped at -78 ¡ã C., and the mixture was stirred for 2 hours and 30 minutes.Dimethylformamide (15.5 mL, 200 mmol) was added thereto, followed by stirring for 1 hour. Then, 3N hydrochloric acid was added, and anhydrous tetrahydrofuran was removed, followed by extraction with chloroform, drying over anhydrous magnesium sulfate, and purification through silica gel (SiO2, n-hexane: ethyl acetate = 5: 1).

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, 1,4-Dibromo-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Korea National University of Transportation Industry Academy Cooperation Foundation; Lee Ji-hun; Choi Yong-seon; Shin Seong-jun; (65 pag.)KR2019/43743; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 858121-94-5, name is 4-(Bromomethyl)-1,1-difluorocyclohexane, 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. Quality Control of 4-(Bromomethyl)-1,1-difluorocyclohexane

General procedure: 2-(4-(ethylsulfonyl)phenyl)-N-(4-((propylamino)methyl)phenyl)acetamide (50 mg, 0.13 mmol) was added sequentially to a 20 mL sealed tube.2-chlorobenzyl bromide (53 muL, 0.4 mmol),Anhydrous potassium carbonate (55 mg, 0.4 mmol),N,N-dimethylformamide 2mL,Heated at 60 C for 3 hours,TLC confirmed that the reaction was completed and washed with saturated brine.Purification of petroleum ether by column chromatography: ethyl acetate 2:1?3:2,Made a white solid 18mg,The yield was 27.8%.

The synthetic route of 4-(Bromomethyl)-1,1-difluorocyclohexane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fudan University; Wang Yonghui; Qiu Ruomeng; Gong Juwen; Tian Jinlong; Huang Yafei; (65 pag.)CN109206346; (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. 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., category: bromides-buliding-blocks

Into a 100 mL three-necked flask were added 4.62 g 1-bromo-2,4,5-trifluorobenzene (0.022 mol) and anhydrous tetrahydrofuran (50 mL). The resulting mixture was cooled to -20 C. The solution of isopropylmagnesium bromide (22 mmol) in tetrahydrofuran (22 ml, 1M THF) was slowly added dropwise under nitrogen. After the addition was complete, the reactants were maintained at -20 C. for later use. Cuprous bromide-dimethyl sulfide (0.41 g, 0.002 mol) was suspended in 5 ml anhydrous tetrahydrofuran. The resulting mixture was cooled to -5 C. The Grignard reagent as described above was slowly added dropwise under nitrogen. After 15 min, a solution of the aziridine compound as shown in the above reaction formula (4.54 g, 0.015 mol) in 30 mL tetrahydrofuran was slowly added dropwise. After additional 5 min, 50 mL saturated solution of ammonia chloride was added to quench the reaction. Into this obtained solution was added 50 mL ethyl acetate. The separated water layer was extracted with another 50 mL ethyl acetate. The obtained organic layers were collected together and further washed with saturated solution of sodium chloride and then dried over anhydrous sodium sulfate, followed by filtration and concentration to obtain a crude product, which was further treated by column chromatography to obtain a compound (5.07 g, 0.012 mol, yield 78%). 1H NMR (400 MHz, CDCl3) delta 7.03 (t, J=10.5 Hz, 1H), 6.91 (t, J=10.7 Hz, 1H), 5.14 (d, J=12.6 Hz, 1H), 3.973.85 (m, 1H), 3.82 (d, J=6.2 Hz, 1H), 3.773.55 (m, 1H), 2.82 (s, 2H), 1.871.68 (m, 1H), 1.631.48 (m, 1H), 1.39 (s, 9H), 0.91 (s, 9H), 0.06 (d, J=4.6 Hz, 6H). Ms (M++1): 434.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 327-52-6.

Reference:
Patent; ZHEJIANG HISOAR PHARMACEUTICAL CO., LTD.; Pan, Xianhua; Li, Weijin; Zhang, Qunhui; Ruan, Libo; Yu, Wansheng; Deng, Fei; Ma, Tianhua; Huang, Mingwang; He, Minhuan; US2013/281695; (2013); 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. 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 138526-69-9

[10092] (1-1) In a nitrogen atmosphere, a solution prepared by dissolving 50 g of 3,4,5-trifluorobromobenzene in 50 mL of THF was added dropwise at a rate that caused gentle reflux to a mixed solution of 6.34 g of magnesium and 60 mL of THF. Afier dropwise addition, the mixture was stirred at 40 C. for 1 hout Then, a solution prepared by dissolving 34.64 g of DMF in 60 mL of THF was added dropwise under ice cooling at such a rate that the inside temperature did not exceed 20 C., followed by stirring at room temperature for 1 hout Then, 10% hydrochloric acid was added until the reaction system became acidic, and the mixture was stirred at room temperature for 1 hout Then, hexane was added to the mixture to separate an organic layer, and an aqueous layer was subjected to extraction with hexane. The hexane extract was combined with the organic layer and washed with a saturated aqueous sodium bicarbonate solution and saturated brine. The resultant mixture was dried by adding sodium sulfate, and then the solvent was distilled off under reduced pressure to yield 37.91 g of 3,4,5-trifluorobenzaldehyde.

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; DIC CORPORATION; Tojo, Kenta; Takeuchi, Kiyofumi; Osawa, Masashi; Kaneoya, Masakazu; Kusumoto, Tetsuo; US2014/275577; (2014); 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. 583-70-0, name is 2,4-Dimethylbromobenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H9Br

Step 2: to a suspension of magnesium powder (239 mg, 9.79 mmol) in dry THF (small amount) was added dropwise 1 -bromo-2,4-dimethylbenzene (1.64 g, 8.86 mmol) diluted in dry THF (20 mL) and the reaction was heated at 40C. After completion of Grignard reagent, 2-methyl-N-[(5-methylfuran-2-yl)methylidene]propane-2-sulfinamide Ex.8a (995 mg, 4.66 mmol) diluted in THF Ex.8b (10 mL) was added to the solution. The reaction mixture was stirred at rt overnight. Water was added to quench the reaction. The two layers were partitionated and the organic layer was dried over MgSO4, filtered and the solution was concentrated under reduced pressure. The crude material was purified by silica gel column chromatography using a gradient of hexanes/EtOAc ([5:1 ] to [4:1 ]) to afford N-[(2,4-dimethylphenyl)(5-methylfuran-2-yl)methyl]-2-methylpropane-2-sulfinamide (1.27 g, 85%) as yellowish oil.

According to the analysis of related databases, 583-70-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; BONNET, Pascal; FOGHA, Jade; (76 pag.)WO2018/138356; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 51554-93-9, name is 1-Bromo-4-octylbenzene, 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 51554-93-9, Quality Control of 1-Bromo-4-octylbenzene

a) Synthesis of 4-bromophenyl 1-pinacolylboronate 50.0 g (186 mmol) of 4-n-octyl bromide, 51.9 g (204 mmol) of bispinacolatodiboron, 52.9 g (539 mmol) of potassium acetate are suspended in 800 ml of dimethyl sulfoxide. 4.55 g (5.6 mmol) of 1,1-bis(diphenylphosphino)ferrocenedichloropalladium(II)*DCM are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, 600 ml of ethyl acetate and 400 ml of water are added, and the organic phase is separated off, washed three times with 200 ml of water, dried using sodium sulfate and subsequently evaporated to dryness. The crude product is recrystallised from heptane and finally dried under reduced pressure. The yield is 48.2 g (152 mmol), corresponding to 82.0% of theory.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Merck Patent GmbH; Buchholz, Herwig; Pan, Junyou; Anemian, Remi Manouk; (27 pag.)US9822299; (2017); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1435-52-5, 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. 1435-52-5, name is 1,4-Dibromo-2-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 6.12 1,4-Di(3′-chlorophenyl)-4-fluorobenzene (7l): Starting with 6 (200 mg, 0.79 mmol), Cs2CO3 (385 mg, 1.81 mmol), Pd(PPh3)4 (3 molpercent), 3-chlorophenylboronic acid (246 mg, 1.58 mmol) and 1,4-dioxane (4 mL), 7l was isolated as a colorless solid (201 mg, 80percent). Mp 102-103 ¡ãC. 1H NMR (300 MHz, CDCl3): delta = 7.25-7.33 (m, 5H, ArH), 7.34-7.35 (m, 1H, ArH). 7.37-7.43 (m, 3H, ArH), 7.49-7.52 (m, 2H, ArH). 13C NMR (75 MHz, CDCl3): delta = 114.8 (d, J = 25.7 Hz, CH), 123.0 (d, J = 4.0 Hz, CH), 125.1 (CH), 127.1 (2CH), 128.0 (d, J = 9.4 Hz, 2CH), 129.0 (d, J = 4.0 Hz, CH), 130.0 (d, J = 33.7 Hz, 2CH), 131.0 (d, J = 4.0 Hz, CH), 134.4 (C), 134.9 (C), 137.0 (C), 141.1 (C), 141.4 (C), 141.5 (C), 159.9 (d, JCF = 248.8 Hz, CF). 19F NMR (282 MHz, CDCl3): delta = -114.6 (CF). IR (ATR, cm-1): , 2923 (w), 2851 (w), 1619 (m), 1562 (m), 1463 (m), 1386 (s), 1288 (m), 1248 (m), 1186 (m), 1130 (m), 1079 (m), 1022 (m), 967 (m), 915 (m), 876 (m), 824 (m), 773 (s), 756 (s), 686 (s), 636 (m), 552 (m), 515 (m), 468 (m), 419 (m) cm-1. GC-MS (EI, 70 eV): m/z (percent) = 292 (100) [M]+, 277 (34), 249 (23), 233 (12). HRMS (EI) calcd. for C18H11Cl2F [M]+: 316.02164; found 316.021941; calcd. for C18H11Cl37ClF [M]+: 318.01869; found 318.01898.

The synthetic route of 1,4-Dibromo-2-fluorobenzene 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, Tama?s; Villinger, Alexander; Langer, Peter; Journal of Fluorine Chemistry; vol. 146; (2013); p. 19 – 36;,
Bromide – Wikipedia,
bromide – Wiktionary