Bromides-buliding-blocks

10016-52-1, A common compound: 10016-52-1, name is 2,8-Dibromodibenzo[b,d]furan, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

In a nitrogen atmosphere, a flask containing 2,8-dibromodibenzo[b,d]furan (2.5 g), (10-phenylanthracen-9-yl) boronic acid (5.7 g), Pd-132 (0.27 g), tetrabutylammonium bromide (0.25 g), potassium carbonate (3.2 g), water (10 ml), and toluene (100 ml) was stirred at a reflux temperature for two hours. The reaction liquid was cooled to room temperature and subjected to liquid separation. The obtained organic layer was washed with water. This solution was decolorized using silica gel and concentrated under reduced pressure. The precipitated solid was washed with heptane to obtain compound (2A-201) (2.5 g). The structure of the compound thus obtained was identified by an NMR analysis. 1H-NMR (400 MHz, CDCl3):delta=8.06?8.05 (m,2H), 7.93?7.90 (m,2H), 7.77?7.70 (m,8H), 7.65?7.55 (m,8H), 7.55?7.47 (m,4H), 7.36?7.31 (m,8H).

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, 2,8-Dibromodibenzo[b,d]furan, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kwansei Gakuin Educational Foundation; JNC Corporation; HATAKEYAMA, Takuji; TAJIMA, Akio; BABA, Daisuke; FUJITA, Yukihiro; YAMAGA, Yuko; IMAI, Hiroyuki; (139 pag.)US2019/312207; (2019); A1;,
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2044-08-8, 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. 2044-08-8, name is 1-Bromocyclohex-1-ene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Add 20 g (0.12 mol) of 1-bromo-1-cyclohexene to a three-necked flask under nitrogen atmosphere.34.7 g (0.14 mol), 2.0 g (6 mol%) of triphenylphosphine,Trans-bis(triphenylphosphine)palladium dichloride (II)2.6 g (3 mol%), potassium phenate 24.6 g (0.19 mol) andAnhydrous toluene 250 mL.After nitrogen substitution, the reaction was stirred at 50 C for 5 hours.The system was then cooled to room temperature and quenched with water.The reaction mixture was extracted with a benzene solvent and brine.The organic phase was dried over anhydrous magnesium sulfate.The dried mixture was filtered and concentrated under reduced pressure.Purified by silica gel column or distillation21.9 g (yield: 85%) cyclohexene-1-boronic acid pinacol ester

The synthetic route of 1-Bromocyclohex-1-ene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yurui (Shanghai) Chemical Co., Ltd.; Zheng Xianzhe; (52 pag.)CN109206456; (2019); A;,
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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. 202865-83-6, name is 1-Bromo-3-fluoro-5-methylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 202865-83-6

Intermediate 157: 4-Fluoro-2-methyl-benzaldehvde; A solution of 10 g of 5-Bromo-3-fluorotoluene (0.05 mole) in 500 mL of THF was cooled to -780C. Then, 32 mL of a solution of n-Butyl lithium in hexanes (2.5 M, 0.08 mole) were added to the mixture keeping the internal temperature between -75C and -78C. The resulting mixture was stirred at -780C for 50 min. 43 mL of Dry DMF (0.53 mole) were added over 1 h to the mixture. The mixture was allowed to warm to RT (about 180C) and stirred overnight. The reaction was quenched with 20 mL of a saturated solution of NH4CI. The mixture was washed with water (5×100 mL) and the organic layer was washed with a 50 mL of a saturated aqueous solution of NaHCO3, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by a column chromatography on silica gel (PE/AcOEt=50/1 ) to give the title compound as light yellow liquid (3.0Og, 41.09%).

The synthetic route of 202865-83-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/148853; (2008); A1;,
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These common heterocyclic compound, 955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan, 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. 955959-84-9

To a 250 mL round bottom flask was added 4-phenylaniline (1.80 g, 10.64 mmol), D1 (3.78 g, 11.70 mmol), Tris (dibenzylideneacetone) dipalladium (0) (0.15 g, -Bis (diphenylphosphino) -1,1′-binaphthalene (BINAP) (0.20 g, 0.32 mmol) and sodium tert-butoxide (1.43 g, 14.89 mmol) were dissolved in toluene (100 mL) After completion of the reaction, the reaction mixture was stirred for 24 hours. Toluene was removed, and the residue was extracted with dichloromethane and water. The residue was subjected to vacuum distillation. The silica gel column was distilled under reduced pressure to obtain Compound D2 (3.05 g, 7.41 mmol).

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 955959-84-9.

Reference:
Patent; LG Display Co., Ltd.; Lee Seung-jae; Pin Jong-gwan; Seo Bo-min; Ryu Yeong-ju; (41 pag.)KR2018/60582; (2018); A;,
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A common heterocyclic compound, 1647-26-3, name is 1-Bromo-2-cyclohexylethane, molecular formula is C8H15Br, 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. 1647-26-3.

60% sodium hydride (526 mg, 0.013 mol) were added portion wise to a mixture of isatin (1.75 g, 0.012 mol) dissolved in 35 mL of dimethylformamide. The reaction medium was stirred at room temperature for 2 hours. A solution of l-Bromo-2- cyclohexylethane (2.5 g, 0.013 mol) dissolved in dimethylformamide (3 mL) was then added drop wise. The reaction medium was stirred at room temperature overnight. After extraction with ethyl acetate, the organic layer was washed with hydrochloric acid (0.4 N) and water. The organic fraction was dried over MgSO4 and concentrated under vacuum. The title compound was prepared as an orange solid following Method A. The resulting solid was washed with a mixture of heptane/AcOEt. Yield: 100%. 1H NMR (CDCl3): delta 0.92-1.05 (m, 2H), 1.12-1.41 (m, 4H), 1.57 (q, J = 6.9Hz, 2H), 1.63-1.82 (m, 5H), 3.74 (t, J = 7.6 Hz, 2H), 6.88 (d, J = 7.8 Hz, IH), 7.11 (t, J = 7.5 Hz, IH), 7.56 – 7.61 (m, 2H). 13C NMR (CDCl3): delta 26.09 (CH2), 26.4 (CH2), 33.08 (CH2), 34.42 (CH2), 35.42 (CH), 38.21 (CH2), 110.12 (CH), 117.66 (C), 123.57 (CH), 125.41 (CH), 138.3 (CH), 151.01 (C), 158.03 (C=O). 178.71 (C=O).

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

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; WO2009/12227; (2009); A1;,
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327-52-6, A common heterocyclic compound, 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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.

[0131] Into a 100 mL three- necked flask were added 4.62 g 1- bromo- 2, 4, 5- trifluorobenzene (0.022 mol) andanhydrous tetrahydrofuran (50 mL) . The resulting mixture was cooled to- 20 C. The solution of isopropylmagnesiumbromide (22 mmol) in tetrahydrofuran (22 ml, 1 M THF) was slowly added dropwise under nitrogen. After the additionwas complete, the reactants were maintained at- 20 C for later use.[0132] Cuprous bromide – dimethyl sulfide (0.41 g, 0.002 mol) was suspended in 5 ml anhydrous tetrahydrofuran. Theresulting mixture was cooled to -5 C. The Grignard reagent as described above was slowly added dropwise undernitrogen. After 15 min, a solution of the acridine compound as shown in the above reaction formula (4.16 g, 0.015 mol)in 30 mL tetrahydrofuran was slowly added dropwise. After additional 5 min, 50 mL saturated solution of ammoniachloride was added to quench the reaction. Into this obtained solution was added 50 mL ethyl acetate. The separatedwater layer was extracted with another 50 mL ethyl acetate. The obtained organic layers were collected together andfurther washed with saturated solution of sodium chloride and then dried over anhydrous sodium sulfate, followed byfiltration and concentration to obtain a crude product, which was further treated by column chromatography to obtain acompound (5.41 g, 0.0132 mol, yield 88%).1H NMR (400 MHz, CDCl3) delta7.53?7.22 (m, 5H), 7.05 (t, J = 10.5 Hz, 1 H), 6.93 (t, J = 10.7 Hz, 1 H), 5.12 (d, J = 12.6Hz, 1H), 3.97?3.85 (m, 1 H), 3.82 (d, J = 6.2 Hz, 1 H), 3.77?3.55 (m, 1H), 3.51 (s, 2H),2.82 (s, 2H), 1.87?1.68 (m, 1H),1.63?1.48 (m, 1 H), 1.39 (s, 9H). Ms (M++1): 410.

The synthetic route of 327-52-6 has been constantly updated, and we look forward to future research findings.

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; EP2647624; (2013); A1;,
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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. 3814-30-0, name is (Bromomethyl)cyclopentane, This compound has unique chemical properties. The synthetic route is as follows., 3814-30-0

EXAMPLE 65 1-Cyclopentylmethyl-3-methyl-6-(4-pyridyl)pyrazolo[3,4-d]pyrimidin-4-amine To a solution of 3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-amine (6.0 g, 0.027 mol) in DMF (50 ml) at 0 C. was added 60% NaH/mineral oil dispersion (1.06 g, 0.027 mol) in one portion. The reaction mixture was warmed to room temperature and stirred for 1 hour. The reaction mixture was cooled to 0 C. and cyclopentylmethyl bromide (4.3 g, 0.027 mol) was added dropwise over 5 minutes. The reaction mixture was warmed to room temperature and stirred for 50 hours. The solvent was removed in vacuo, the yellow slurry was added to water (100 ml) and acidified with acetic acid. The resulting paste was stripped to dryness and the residue was slurried with ethanol. A tan solid was collected by filtration and purified by column chromatography on silica eluding with ether/ethanol/water (97.5/2/0.5) followed by recrystallization from cyclohexane to afford 2.2 g (26%) of 1-cyclopentylmethyl-3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d] -pyrimidin-4-amine, m.p. 177-178 C.

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; Sterling Winthrop Inc.; US5294612; (1994); A;,
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22385-77-9, 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 22385-77-9 as follows.

To a solution of 1-bromo-3,5-di-tert-butylbenzene (527 mg, 1.96 mmol) in Et2O (10mL) at -78 C under N2 atmosphere was added dropwise n-BuLi (1.65 M in hexane, 1.1mL, 1.82 mmol). The resulting solution was warmed to room temperature and stirredfor 1 h. This solution was added dropwise to a solution of5,15-bis(triisopropylsilylethynyl)porphyrin2 (200 mg, 298 mumol) in dry THF (10 mL).After the mixture was stirred at room temperature overnight, water (1.0 mL) and thenDDQ (204 mg, 90.0 mumol) were added. The reaction mixture was stirred for additional 20 min before addition of triethylamine (0.2 mL). The volatiles were removed in vacuoand the residue was taken up in CH2Cl2 and washed with water and brine. The organiclayer was dried over Na2SO4 and concentrated. The residue was separated by silica-gelcolumn chromatography (CH2Cl2/hexane=1/4 as an eluent). After removal of thesolvent in vacuo, recrystallization from CH2Cl2/MeOH gave 5 (195 mg, 227 mumol) in76% yield as a purple solid. 1H NMR (400 MHz, CDCl3, RT): delta = 10.06 (s, 1H,meso-H), 9.72 (d, J = 4.4 Hz, 2H, beta-H), 9.64 (d, J = 4.8 Hz, 2H, beta-H), 8.87 (d, J = 4.8Hz, 2H, beta-H), 7.99 (d, J = 1.6 Hz, 2H, Ar-o), 7.81 (t, 2H, J = 1.8 Hz, Ar-p), 1.53 (s, 18H,tBu), 1.47 (s, 18H, tBu), 1.44 (s, 18H, tBu), and -2.40 (br, 2H, NH) ppm; 13C NMR(126 MHz, CDCl3): delta = 148.8, 140.7, 129.4 (br), 129.3, 123.7, 121.4, 106.2, 100.5,99.27, 35.0, 31.7, 19.1, 12.1, and 11.8 ppm; HR-MS (ESI): m/z = 859.5579 calcd for(C56H75N4Si2)+ = 859.5525 [(M+H)+].

According to the analysis of related databases, 1-Bromo-3,5-di-tert-butylbenzene, the application of this compound in the production field has become more and more popular.

Reference:
Article; Takiguchi, Asahi; Wakita, Mana; Hiroto, Satoru; Shinokubo, Hiroshi; Chemistry Letters; vol. 48; 4; (2019); p. 371 – 373;,
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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. 34699-28-0, name is 1-(4-Bromophenyl)-1,2,2-triphenylethylene, A new synthetic method of this compound is introduced below., 34699-28-0

theTetraphenylethylene bromide (4.11g,10.0mmol) and 4-Formylphenylboronic acid(1.49g,10.0mmol)added into three necked flask, then added 60m of toluene , 15ml of 2M K2CO3aqueous solution, Tetrabutyl ammonium bromide (TBAB)(0.64g,2.0mmol), after passing the Argon for 40 min, a amount ofcatalyst Pd (PPh3)4 added , oil bath was heated to 85 Cfor 24 h. The reaction was terminated, extraction was carried out with water,afterorganic phase was dried over anhydrous sodium sulfate and dried in vacuo on arotary evaporator to give the crude product. The product was purified by silicagel column chromatography; the eluent was a mixed solvent of dichloromethaneand n-hexane with volume ratio of 10:1 and 1:1. Pure product as a beige solid,3.3 g (yield 76%).

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; Sun Yat-sen University; Ma, ChunPing; Chi, ZhenGuo; Zhou, Xie; Zhang, Yi; Liu, SiWei; Xu, JiaRui; (14 pag.)CN103804318; (2016); B;,
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The chemical industry reduces the impact on the environment during synthesis 58971-11-2, name is 3-Bromophenethylamine, I believe this compound will play a more active role in future production and life. 58971-11-2

To a solution of methanesulfonyl chloride(1.60 mmol, 0.12 mL, 1.0 equiv) in ethanol (3 mL), 2-(3-bromophenyl)ethan-1-amine (3.20 mmol, 639mg, 2.0 equiv) was added and the mixture was stirred at room temperature. The reaction wasmonitored by TLC. After completion the solvent was removed under reduced pressure and theremaining solid dissolved in a small amount of water. The solution was applied to a C18 precolumnbefore purification on a 60 g C18 column with a gradient of acetonitrile in water (10-80%). The titlecompound (1.07 mmol, 295 mg, 66%) was obtained as a white solid.

The chemical industry reduces the impact on the environment during synthesis 58971-11-2. I believe this compound will play a more active role in future production and life.

Reference:
Article; Akhter, Sundus; Lund, Bjarte Aarmo; Ismael, Aya; Langer, Manuel; Isaksson, Johan; Christopeit, Tony; Leiros, Hanna-Kirsti S.; Bayer, Annette; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 634 – 648;,
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