Tag: M.W=300-400

Application of 927384-44-9, 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 927384-44-9 as follows.

Bromo-1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-benzene 11 (2.40 g, 7.43 mmol), 4-(ethoxycarbonyl)phenylboronicacid 12 (2.40 g, 12.4 mmol), powdered tripotassium phosphate(3.40 g, 20.7 mmol) and 1,4-dioxane (150 cm3) were added to around-bottom flask fitted with a condenser and heated at 80 Cfor 15 min under N2. Pd(PPh3)4 (0.47 g, 0.41 mmol) was added tothe mixture which was purged with N2 for a further 15 min beforebeing stirred at 80 C for 2 days. The mixture was allowed to cool,filtered and the filtrate concentrated under reduced pressure. Theresulting residue was dissolved in chloroform (100 cm3), washedwith water (3 x 50 cm3) and brine (50 cm3) and concentratedunder reduced pressure to give a brown solid, which wasrecrystallised from chloroform and methanol to give 13 as largeyellow needles (yield 2.07 g, 71%). 1H NMR (CDCl3, 400 MHz) delta 8.25-8.04 (m, 2H), 7.85-7.67 (m, 6 H), 7.19 (dd, J = 7.3, 8.2 Hz,2H), 7.11 (d, J = 7.8 Hz, 2H), 6.48 (dd, J = 0.8, 7.3 Hz, 2H), 6.11 (s,2 H), 4.45 (q, J = 7.2 Hz, 2H), 1.46 (t, J = 7.2 Hz, 3H). ESI-TOF-MS:m/z 392.23 [M]+. Elemental Anal. Calc. for C25H21BN2O2: C, 76.55;H, 5.40; N, 7.14. Found: C, 76.51; H, 5.33; N, 7.26%. ATR-FTIR(cm-1): 3360 (s), 2900 (m), 1590 (s), 1580 (s), 1360 (m), 1260(s), 1080 (m), 756 (m, br), 728 (m).

According to the analysis of related databases, 927384-44-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Argent, Stephen P.; Tarassova, Irina; Greenaway, Alex; Nowell, Harriot; Barnett, Sarah A.; Warren, Mark R.; Tang, Chiu C.; Morris, Christopher G.; Lewis, William; Champness, Neil R.; Schroeder, Martin; Blake, Alexander J.; Polyhedron; vol. 120; (2016); p. 18 – 29;,
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10016-52-1, name is 2,8-Dibromodibenzo[b,d]furan, 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. Product Details of 10016-52-1

250mL 2 necked flask equipped with a 10-phenyl-2 ‘- (4,4,5,5-tetra-methyl -1,3,2-dioxa-beam as is -2 yl) -10H- spiro [acridine -9,9’- fluorene] (3g, 5.62mmol), 2,8- di-bromo-modify-benzo [b, d] furan (2,8-dibromodibenzo [b, d] furan) (0.95 g, 2.25 mmol) , tetrakis (triphenylphosphine) palladium (0) (0.13g, 0.112 mmol), potassium carbonate (1.5g, 11.2mmol), tetrahydrofuran: water (3: 1) is dissolved in the mixture was stirred under reflux.After 12 hours After cooling to room temperature, extracted with dichloromethane, and then after drying the water with magnesium sulfate to remove the solvent.Hexane: ethyl acetate (10: 0.5) and the column with the solvent, to filter the resulting solid was precipitated with petroleum ether to give a white solid Compound B 1.5g (68% yield)

The synthetic route of 10016-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG DISPLAY CO., LTD.; Bae, Sook Young; Song, In Bum; Yun, Gyung Jin; Lee, Sang Ho; Noh, Hyo Jin; Yun, Dae Wei; Haw, Hay Ryong; Kim, Chun Gi; (17 pag.)KR2015/65385; (2015); A;,
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Reference of 955959-84-9,Some common heterocyclic compound, 955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan, molecular formula is C18H11BrO, 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.

In a stream of argon, 185 g of 1-acetamide (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.), 323 g of Intermediate 1-6 (manufactured by Wako Pure Chemical Industries, Ltd.), 544 g of potassium carbonate (manufactured by Wako Pure Chemical Industries, Ltd.), 12. 5 g of a copper powder (manufactured by Wako Pure Chemical Industries, Ltd.), and 2 L of decalin were loaded and subjected to a reaction at 190°C for 4 days. After the reaction, the resultant was cooled, and then 2 L of toluene were added to the resultant. The insoluble portion was taken by filtration. The product taken by filtration was dissolved in 4.5 L of chloroform, and then the insoluble portion was removed. After that, the remainder was subjected to an activated carbon treatment and concentrated. 3 liters of acetone were added to the resultant, and then 181 g of the precipitated crystal were taken by filtration. The crystal was identified as Intermediate 1-15 by FD-MS analysis.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-Bromophenyl)dibenzo[b,d]furan, its application will become more common.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2364980; (2011); A1;,
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Related Products of 3344-70-5, These common heterocyclic compound, 3344-70-5, name is 1,12-Dibromododecane, 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.

1.0 g of compound 3,2.63 g of 1,12-dibromododecane,0.43 g of potassium hydroxide and 0.16 g of tetrabutylammonium bromide,Was added to a mixture of 10 ml of dichloromethane and 6.5 ml of water,The mixture was stirred at room temperature under nitrogen for 24 hours,Washed twice with 30 ml of water,Washed once with 15 ml of saturated brine,The organic layer was separated,After adding anhydrous sodium sulfate to remove water,The solvent was removed on a rotary evaporator,(200: 300 mesh silica gel column chromatography elution (ethyl acetate / petroleum ether volume ratio of l: 30-l: 10),To give 1.19 g of the compound 4 as a pale yellow liquid,Yield 90percent.

Statistics shows that 1,12-Dibromododecane is playing an increasingly important role. we look forward to future research findings about 3344-70-5.

Reference:
Patent; Guilin University of Technology; Kong, Xiangfei; Dai, Shengping; Chang, Xiao; Zhang, Laiqi; Wang, Guixia; (10 pag.)CN106117220; (2016); A;,
Bromide – Wikipedia,
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These common heterocyclic compound, 10016-52-1, name is 2,8-Dibromodibenzo[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. name: 2,8-Dibromodibenzo[b,d]furan

1b) 2,8-Bis-((E)-styryl)-dibenzofuran Tetrethylamine hydroxide (13.6 g, 18.4 mmol), tetrakis(triphenylphosphine)palladium(0) (142 mg) and trans-2-phenylvinylboronic acid (2.3 g, 15.3 mmol) are added to a solution of the product from example 1a) (2.00 g, 6.14 mmol) in N,N’-Dimethylacetamide (DMA) (30 ml). The mixture is then stirred at 110 C. for 24 hours. The reaction mixture is cooled to room temperature and poured into H2O. A gray crude product is obtained after filtration and washing with n-hexane. The crude product is purified by silicagel column chromatography with CH2Cl2, which result in a white solid (71% yield, mp.: 226 C.). 1H-NMR (CDCl3, ppm): 7.26-7.30 (m, 6H), 7.39 (t, 4H), 7.54-7.58 (m, 6H), 7.65 (dd, 2H), 8.12 (d, 2H)

The synthetic route of 2,8-Dibromodibenzo[b,d]furan has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tanabe, Junichi; Oka, Hidetaka; Yamamoto, Hiroshi; US2009/131673; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 10016-52-1, name is 2,8-Dibromodibenzo[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. Recommanded Product: 2,8-Dibromodibenzo[b,d]furan

General procedure: 3.26 g of 2,8-dibromodibenzofuran, 1.9 g of pyridin-2-ol, 0.2 g of CuI, 0.2 g of 1,10-phenanthroline, and 6.3 g of K3PO4 were added to 200 mL of dimethylformamide (DMF) and stirred at a temperature of 160 C. for 24 hours. After cooling, 400 mL of a mixed solution including brine ice was added thereto, and a reaction mixture was precipitated, filtered, and washed with water. An organic layer obtained therefrom by washing the reaction mixture with ethyl acetate and water three times was dried by using MgSO4 and dried under reduced pressure. Column chromatography was used to obtain 1.77 g (yield: 50%) of Intermediate 1-1.

The synthetic route of 2,8-Dibromodibenzo[b,d]furan has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung Display Co., Ltd.; SIM, Munki; KO, Soobyung; KIM, Sungbum; PARK, Junha; AHN, Heechoon; LEE, Hyoyoung; JEON, Mina; JUN, Mieun; HAN, Junghoon; KIM, Youngkook; HWANG, Seokhwan; (93 pag.)US2019/296253; (2019); A1;,
Bromide – Wikipedia,
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52997-43-0, name is 7-(Bromomethyl)pentadecane, 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. category: bromides-buliding-blocks

Di-tert-butyl thieno[3,2-b]thiophene-3,6-diyldicarbamate (20) (0.93 g, 2.5 mmol, 1.0 e.q.) wasdissolved in DMF (25 mL) and cooled to 0C. Sodium hydride (0.40 g, 60% dispersion in mineral oil, 10.0 mmol, 4.0 e.q.) was added and the solution was stirred at room temperature for 1hour. 7-(bromomethyl)pentadecane (2.29 g, 7.5 mmol, 3.0 e.q.) was added to the mixture and the solution was stirred at 80C for 3 hours. After the solution cooled to room temperature, the mixture was poured into iced water, followed by extraction with ethyl acetate for three times.The organic layers were combined, washed with water, brine and then dried over Mg504, concentrated. The resulting brown oil was purified via silica gel column chromatography with di15 chloromethane/petroleum ether (1:1) as the eluentto give di-tert-butyl thieno[3,2-b]thiophene-3,6-diylbis((2-hexyldecyl)carbamate) as a light brown oil (21) (1.64 g, 2.0 mmol, 80 % yield). 1HNMR (400 MHz, CDCI3) 67.04 (s, 2H), 3.62 (d, J= 7.2 Hz, 4H), 1.58-1.48 (m, 2H), 1.34-1.11(m, 48H), 0.87 (q, J= 6.8 Hz, 12H). 13C NMR (101 MHz, CDCI3) 6 154.13, 134.76, 133.70,119.18, 80.64, 53.38, 36.93, 31.90, 31.77, 31.21, 30.03, 29.68, 29.52, 29.29, 28.15, 26.31,26.25, 22.66, 22.62, 14.08.

The synthetic route of 52997-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; FLORES, Jean-Charles; HAYOZ, Pascal; MCCULLOCH, Iain; ONWUBIKO, Nkechinyerem; KAELBLEIN, Daniel; (65 pag.)WO2017/148864; (2017); A1;,
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Electric Literature of 2789-89-1,Some common heterocyclic compound, 2789-89-1, name is 1,2-Bis(4-bromophenyl)ethyne, molecular formula is C14H8Br2, 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.

In 25mL dry pressure reaction tube, was added 58mg of 1-octyl-4- (p-chlorophenyl) -1,2,3-triazole, 134mg of 1-phenyl-1-propyne, 6mg of dichloro (pentamethylcyclopentadienyl yl) rhodium dimer, 80mg of copper acetate monohydrate, 32mg 1.5mL sodium peroxide and 1,2-dichloroethane.100 stirred for 24 hours.After the reaction was cooled to room temperature, directly on a silica gel column (ethyl acetate and petroleum ether, the volume ratio of 1: 3) to give product 48mg, 39% yield,

The synthetic route of 2789-89-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University; Chen, Wanzhi; (11 pag.)CN104725375; (2016); B;,
Bromide – Wikipedia,
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Application of 201138-91-2, 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. 201138-91-2, name is 4,6-Dibromodibenzo[b,d]furan, This compound has unique chemical properties. The synthetic route is as follows.

0.1 mol of 4,6-dibromodibenzofuran was dissolved in 320 ml of 1,4-dioxane solvent.Stirring with nitrogen,Add 0.09 mol of [4-(triphenylsilyl)phenyl]boronic acid,0.25 mol of potassium carbonate,0.0001 mol of tetrakis(triphenylphosphine)palladium,Warming up to reflux reaction,After 5 hours, the basic reaction of the raw materials was determined by HPLC.The reaction solution was dried under reduced pressure.The residue was subjected to column chromatography to give Intermediate 1-9-1. (Yield: 63%)

The chemical industry reduces the impact on the environment during synthesis 4,6-Dibromodibenzo[b,d]furan. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Beijing Lv Ren Science And Technology Co., Ltd.; Lv Yao; Jia Xueyi; (19 pag.)CN108424420; (2018); A;,
Bromide – Wikipedia,
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Some common heterocyclic compound, 4101-68-2, name is 1,10-Dibromodecan, molecular formula is C10H20Br2, 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. SDS of cas: 4101-68-2

Tempo 1 (0.01 mol) was added to a three-neck flask containing 100 ml dry benzene that is maintained at nitrogen atmosphere. To the flask, sodium hydride (0.015 mol) was added and kept refluxed for 24 hrs. The flask was cooled in ice bath and added 1,10- dibromodecane (0.02 mol) in one portion. The refluxing was then resumed for another 72 hrs. The contents of the flask was cooled in ice bath and added 25ml water and transferred to a separatory funnel. The red upper benzene layer was separated , dried over anhydrous magnesium sulfate and solvent removed by rotory evaporation to get a red oil. The oil was purified by column chromatography on silica gel 60. The material was added to the column and eluted first with about 150 ml hexane that removed the excess of dibromodecane. The desired bromodecanoyl ether of Tempol was eluted with a mixture of hexane and ether(90:10). The red eluate was collected and was found to be pure on thin layer chromatography plates developed using the same solvent mixture. The yield was 0.008 mol (80%).The bromoether of Tempol 0.008 mol and triphenyl phosphine (0,01 mol) were taken in a flask and added 20ml of n-propanol. The contents of the flask was kept refluxed under nitrogen for 72 hrs. The flask was cooled and the solvent was removed by rotory evaporation. The residue was dissolved in 10 ml dichloromethane and added to 100 ml ether with stirring. The precipitated product was collected by decantation of the solvent. The residual semisolid was then purified on silica gel 60 column eluting first with dichloromethane and the desired product was ehited with a mixture of dichloromethane and methanol (90:10). Homogeneous fractions combined and solvent removed to get a red-brown semisolid with a yield of 65%. Purity was ascertained by LC-MS (mass =573.4) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4101-68-2, its application will become more common.

Reference:
Patent; COLBY PHARMACEUTICAL COMPANY; MEDICAL COLLEGE OF WISCONSIN, INC.; WO2008/109740; (2008); A2;,
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