Tag: M.W=200-300

Related Products of 101-55-3, These common heterocyclic compound, 101-55-3, name is 1-Bromo-4-phenoxybenzene, 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.

To a solution of compound 55-1 (16 g, 64 mmol) in TEA (160 mL) was added PPh3 (1.68 g, 6.4 mmol), cuprous iodide (0.6 g, 3.2 mmol), palladium acetate (0.72 g, 3.2 mmol) and trimethylchlorosilane (10.7 g, 96 mmol) and the reaction solution was stirred at 90 C. for 12 h, after which water (100 mL) was added and the resulting solution was extracted with EtOAc (100 mL×4). The organic phases were combined, dried over anhydrous Na2SO4, filtered and evaporated to give a crude product which was purified by column chromatography to afford the title compound 55-2 (yellow solid, 15 g, Yield 88%). 1H NMR (400 MHz, CDCl3): delta ppm 7.45 (d, J=8.78 Hz, 2H), 7.35-7.41 (m, 2H), 7.13-7.19 (m, 1H), 7.04 (d, J=7.78 Hz, 2H), 6.93 (d, J=8.78 Hz, 2H), 0.27 (s, 9H).

Statistics shows that 1-Bromo-4-phenoxybenzene is playing an increasingly important role. we look forward to future research findings about 101-55-3.

Reference:
Patent; Hubei Bio-Pharmaceutical Industrial Technological Institute Inc.; Humanwell Healthcare (Group) Co., Ltd.; Wang, Xuehai; Wu, Chengde; Xu, Yong; Shen, Chunli; Li, Li’e; Hu, Guoping; Yue, Yang; Li, Jian; Guo, Diliang; Shi, Nengyang; Huang, Lu; Chen, Shuhui; Tu, Ronghua; Yang, Zhongwen; Zhang, Xuwen; Xiao, Qiang; Tian, Hua; Yu, Yanping; Chen, Hailiang; Sun, Wenjie; He, Zhenyu; Shen, Jie; Yang, Jing; Tang, Jing; Zhou, Wen; Yu, Jing; Zhang, Yi; Liu, Quan; (251 pag.)US2017/313683; (2017); A1;,
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Synthetic Route of 37895-73-1, 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. 37895-73-1, name is 1,2-Dibromo-4,5-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A 12 mL vial was charged with [Pd(cinnamyl)Cl]2(1,5 mol%), dppp (3 mol%). and a stirring bar. Then, 1,2-dibromo-benzene(0.5 mmol), DBU (4.0 eq) and toluene (3 mL) were injected by syringe underargon. The vial (or several vials) was placed in an alloy plate, which wastransferred into a 300 mL autoclave of the 4560 series from Parr Instrumentsunder argon atmosphere. After flushing the autoclave three times with CO, apressure of 10 bar of CO was adjusted at ambient temperature. Then, thereaction was performed for 16-24 h at 140 oC. After the reactioncompleted, the autoclave was cooled down with ice water to room temperature andthe pressure was released carefully. After evaporation of the organic solventthe residue was adsorbed on silica gel and the crude product was purified bycolumn chromatography using EA/pentane(1:1) for phthalimides and MeOH/EA (1:40) for the amides as eluent.

The chemical industry reduces the impact on the environment during synthesis 1,2-Dibromo-4,5-dimethoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Chen, Jianbin; Natte, Kishore; Wu, Xiao-Feng; Tetrahedron Letters; vol. 56; 2; (2015); p. 342 – 345;,
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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 36805-97-7 as follows. Product Details of 36805-97-7

Example 678-Amino-1 -methyl -4,5-dihydro-1 H-1 ,7,9-triaza-cyclopentafa1naphthalene-2,3- dicarboxylic acid 2-tert-butyl ester 3 -ethyl ester (N6) To a solution of i-methyl^-oxo^AthetaJ-tetrahydro-I H-indole^S-dicarboxylic acid 2-tert- butyl ester 3-ethyl ester XXVIA (4.67 mmol) in DMF (20 ml_), N,N-dimethylformamide di- tert-butyl acetal (2 mL) was added and the solution was stirred at 1000C overnight. After cooling to rt guanidine hydrochloride (14 mmol) and K2CO3 (14 mmol) were added and the mixture was heated at 1000C for 24 h. The organic solvent was evaporated to dryness. Chromatography on silica gel (AcOEt/hexane 1 :1 ) afforded the title compound (80% yield). ESI (+) MS: m/z 373 (MH+). 1H NMR: 1.28 (t, J=7.07, 3H), 1.55 (s, 9H), 2.68 (t, J=7.80, 2H), 2.79 (t, J=7.80, 2H), 4.18 (s, 3H), 4.23 (q, J =7.07, 2H), 6.40 (bs, 2H), 7.97 (s, 1 H).

According to the analysis of related databases, 36805-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; WO2008/65054; (2008); A1;,
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Reference of 2132-62-9,Some common heterocyclic compound, 2132-62-9, name is 1,2-Bis(4-methoxyphenyl)ethyne, molecular formula is C16H14O2, 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: A mixture of a substituted benzamide (1) (0.3 mmol, 1.0 equiv),an alkyne (2) (0.6 mmol or 0.9 mmol, 2.0 equiv or 3.0 equiv),10% Pd/C (0.03 mmol, 10 mol%, Alfa Aesar, No. 044696, eggshell,reduced), NaI·2H2O (0.6 mmol, 2.0 equiv), Cs2CO3 (0.3 mmol, 1.0equiv), and KOAc (0.6 mmol, 2.0 equiv) was weighted in a Schlenktube equipped with a stir bar. DMF (1.0 mL) was added and themixture was stirred at 120 C for 36 h under air. Afterwards, themixture was filtered and washed with H2O (30 mL) and extractedwith CH2Cl2 (3×30 mL). The combined organic phase was driedwith anhydrous Na2SO4. After removal of solvents under reducedpressure, the residue was absorbed to small amounts of silica. Thepurification was performed by flash column chromatography onsilica gel with EA:PE (Petroleum ether) = 1:5 or 1:10 as eluent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Bis(4-methoxyphenyl)ethyne, its application will become more common.

Reference:
Article; Shu, Zhen; Guo, Yuntao; Li, Wei; Wang, Baiquan; Catalysis Today; vol. 297; (2017); p. 292 – 297;,
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Synthetic Route of 2132-62-9, 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. 2132-62-9, name is 1,2-Bis(4-methoxyphenyl)ethyne belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 5 Preparation of 3,4-Bis(4-methoxyphenyl)-1-ethoxybenz[c-1,2]oxaphosphinine 1-oxide 3,4-Bis(4-methoxyphenyl)-1-ethoxybenz[c-1,2]oxaphosphinine 1-oxide (57.0 mg, 90%) as a target compound was obtained under the condition of 90 C. for 12 hours, by the same reaction as the Example 1 above, except for using 1,2-bis(4-methoxyphenyl)ethyne (54.0 mg, 0.23 mmol) instead of using diphenylacetylene of the Example 1 above. 1H NMR (400 MHz, CDCl3) delta 7.95-7.89 (m, 1H), 7.48-7.43 (m, 1H), 7.41-7.37 (m, 1H), 7.19 (dt, J=9.17 Hz, 2.56 Hz, 2H), 7.14-7.10 (m, 2H), 7.00-6.96 (m, 1H), 6.93-6.89 (m, 2H), 7.19 (dt, J=9.20 Hz, 2.52 Hz, 2H), 4.30-4.15 (m, 2H), 3.84 (s, 3H), 3.75 (s, 3H), 1.31 (t, J=4.82 Hz, 3H)

The synthetic route of 1,2-Bis(4-methoxyphenyl)ethyne has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KNU-INDUSTRY COOPERATION FOUNDATION; Lee, Phil Ho; Park, Young Chul; Jeon, In Cheol; Seo, Jung Min; Seo, Bo Ram; US2015/344506; (2015); A1;,
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Application of 332-48-9, 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. 332-48-9 name is 1-(2-Bromoethoxy)-4-fluorobenzene, 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 suspension of N-Boc- (L)-dopa 67.27 mmol), 2-(4- fluorophenoxy) ethyl bromide (0.95 eq) and potasium bicarbonate (1.1 eq) in DMA (100 mL) was stirred at 65 C overnight. The reacted mixture was diluted with EtOAc (750 mL), washed with water (2×200 mL) and saturated NaHC03 (2×200 mL), brined, dried over Na2S04, concentrated under reduced pressure, and purified by column chromatography on silica gel (60 A, 200-400 Mesh) eluting with 3:7 EtOAc/Hexane to give a clear oil. [00176] The oil was dissolved in a solution of HCl/1,4-dioxane (4.OM, 100 mL), and the mixture was stirred at room temperature for 1 hour before concentrating under reduced pressure to a solid. After dissolving the solid in a minimal amount of acetonitrile (100 mL), the solution was chilled to 4 C, and the resulting white precipitate was collected on a Buchner funnel, washed with diethyl ether (3×50 mL) and dried under high vacuum to afford the title compound as a solid: ¹H NMR (d6-DMSO) : No. 2.92 (m, 2H), 4.14 (m, 2H), 4.21 (t, J = 6.4 Hz, 1H), 4.42 (t, J = 4.4 Hz, 2H), 6.43 (d, J = 7.6 Hz, 1H), 6.59 (s, 1H), 6.60 (d, J = 8.0 Hz, 1H), 6.94 (m, 2H), 7.12 (3, 2H), 8.40 (s, 3H), 8.90 (m, 2H). MS (ESI) m/z 336 (M+H) (at) and 334 (M-H)-.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2-Bromoethoxy)-4-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; XENOPORT, INC.; WO2005/121070; (2005); A1;,
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954235-83-7, name is 1-Bromo-2-(difluoromethoxy)-4-fluorobenzene, belongs to ethers-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. Recommanded Product: 954235-83-7

A mixture of l-bromo-2-(difluoromethoxy)-4-fIuorobenzene (intermediate 176a, 70 mg), N-[3- chloro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]-2-[4-(ethylsulfonyl)phenyl]acetamide (intermediate 6b, 148 mg), PdCl2(dppi)-CH2CI2 adduct (18.98 mg) and Cs2C03 (114 mg) in acetonitrile (1.5 mL)/water (0.5 mL) was sealed in a vessel and heated in (lie microwave at 100C for 45 mins. The reaction mixture was filtered through celite and silica gel. The filtrate was concentrated under reduced pressure and the residue was purified by MDAP to afford N-(2-chloro-2′- (difluoromethoxy)-4′-fluoro-[l, -biphenyl]-4-yl)-2-(4-(ethylsulfonyl)phenyl)acetamide (22 mg) as a white solid. ?-NMR (400 MHz, DMSO-<¾ delta ppm 1.10 (t, /= 7.2 Hz, 3H), 3.28 (q, J= 7.2 Hz, 2H), 3.84 (s; 2H), 7.21 (t, J= 73.2 Hz, 1H), 7.21 (m, 2H)} 7.28 (d, J - 8.4 Hz, 1H), 7.37 (m, 1H), 7.53 (dd, J= 2.0 Hz, 8.4 Hz, 1H), 7.62 (d, J= 8.0 Hz, 2H), 7.86 (d, J= 8.4 Hz, 2H), 7.91 (d, J= 2.0 Hz, 1H), 10.55 (s, 1H); 19F-NMR (376 MHz, DMSO-rf6) delta ppm -82.43, -110.64; MSiES4) m/? 498 (MH+). The synthetic route of 954235-83-7 has been constantly updated, and we look forward to future research findings. Reference:
Patent; GLAXO GROUP LIMITED; WANG, Yonghui; CAI, Wei; LIU, Qian; MENG, Qinghua; CHENG, Yaobang; YANG, Ting; ZHANG, Guifeng; XIANG, Jianing; WU, Chengde; WO2013/29338; (2013); A1;,
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Electric Literature of 104197-14-0, 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. 104197-14-0 name is 4-Bromo-2,6-difluoroanisole, 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.

Intermediate 112 2-(3,5-difluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxa borolane To a solution of intermediate 111 (2.0 g, 8.968 mmoles) in Dioxan (40 ml), bis(pinacaloto)diboron (2.73 g, 10.76 mmoles) and potassium acetate (2.64 g, 26.90 mmoles) were added and the system is degassed for 30 min Bis(diphenylphosphinoferrocene)dichloro palladium.CH2Cl2 (0.219 g, 0.269 mmoles) was added under nitrogen atmosphere and heated to 80 C. After 12 h, the reaction mixture filtered through celite and concentrated. The crude product was purified by column chromatography with ethyl acetate:petroleum ether to afford the title compound as yellow liquid (2.2 g, 90% yield).). 1H-NMR (delta ppm, DMSO-d6, 400 MHz): delta delta 7.318 (d, J=8.7 Hz, 2H), 4.02 (s, 3H), 1.32 (s, 12H).

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

Reference:
Patent; Rhizen Pharmaceuticals SA; Incozen Therapeutics Pvt. Ltd.; US2011/118257; (2011); A1;,
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Related Products of 156573-09-0, The chemical industry reduces the impact on the environment during synthesis 156573-09-0, name is 1-Bromo-4-ethoxy-2,3-difluorobenzene, I believe this compound will play a more active role in future production and life.

According to the synthetic scheme shown above, compound (T-2) (129.5 g) obtained as an intermediate of Example 1 was dissolved in DryTHF (500 ml), and the resultant solution was cooled to -70C. In a nitrogen atmosphere, n-BuLi (500 ml) was added dropwise, and agitation was carried out at -70C for 2 hours. Then, a DryTHF solution of trimethyl borate (129.5 g) was slowly added dropwise at -70C, and the resultant solution was heated to room temperature and agitated for 16 hours. After completion of the reaction, 2N-HCl (200 ml) was added, and then extraction was carried out with toluene, an organic layer was washed with water and a saturated aqueous solution of sodium chloride, and then the resultant solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and thus a light brown solid was obtained. The resultant material was subjected to recrystallization (heptane: toluene = 4 : 1 in a volume ratio), and thus (T-20) was obtained as a colorless crystal (117.2 g, yield: 71%).

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-Bromo-4-ethoxy-2,3-difluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JNC Corporation; JNC Petrochemical Corporation; EP2484658; (2012); A1;,
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Application of 19056-40-7, A common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-methoxyaniline, molecular formula is C7H8BrNO, 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.

To a solution of 4-bromo-3-methoxyaniline (1k) (2.00 g, 9.9 mmol) in water (50 mL) was added hydrochloric acid (4 mL) and sodium nitrite , NaNO2) (0.75 g, 10.9 mmol) is slowly added at 0°C. The mixture was stirred at 0 °C for 30 minutes and then potassium carbonate (1.67 g, 11.9 mmol), copper cyanide (CuCN) (1.06 g, 11.9 mmol) and potassium cyanide (KCN) Mmol) dissolved in water (50 mL). The mixture is stirred at 70°C , cooled, and extracted with toluene. Magnesium sulfate is added to the extracted organic layer to remove water and concentrated under reduced pressure. The concentrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane: ether = 6: 1) , 4-bromo-3-methoxybenzonitrile can be obtained in the form of yellow powder.

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; Konkuk University Industrial Cooperation Corp; Chong, Yu-Hun; Park, Kwang-Su; Kim, Mi-Kyung; Kim, Kyung-Do; (20 pag.)KR2017/17173; (2017); A;,
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