Category: ethers-buliding-blocks

Synthetic Route of 104197-14-0, 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. 104197-14-0, name is 4-Bromo-2,6-difluoroanisole belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 14. 2-r3,5-difluoro-4-(methyloxy)phenylH,4,5,5-tetramethyl-1.3,2- dioxaborolane; A solution of 4-bromo-2,6-difluoroanisole (223mg, 1 mmole), bis(pinacaolato)diboron (275 mg, 1.09 mmole), [1 ,1 ‘-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (40 mg) and KOAc (300 mg) in 5 ml of dioxane was heated in the microwave at 150 for 20 minutes. The reaction was diluted with H2O and extracted with Et2O. The extracts were washed with H2O, dried and evaporated. The residue was chromatographed on a Florisil column, and the titled compound was eluted with Et20, 158 mg (58%). 1H NMR (400 MHz, CDCI3) delta 7.32 (d, J=8Hz, 2H), 4.05 (s, 3H), 1.35 (s, 12H).

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, 4-Bromo-2,6-difluoroanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/63167; (2006); A1;,
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Synthetic Route of 53087-13-1, The chemical industry reduces the impact on the environment during synthesis 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, I believe this compound will play a more active role in future production and life.

General procedure: Under a nitrogen gas atmosphere, 3-bromoanisole(35 mL, 277 mmol) was added dropwise to a mixtureof magnesium (7.1 g, 292 mmol) and a catalytic amount ofiodine in tetrahydrofuran (THF) (270 mL), and the mixturewas stirred for 2 h. This reaction solution was added dropwiseto a solution of tert-butyl (2S)-2-{[methoxy(methyl) amino]-carbonyl}piperidine-1-carboxylate (8, 50.0 g, 184 mmol) inTHF (300 mL) under ice cooling, and the mixture was stirredat room temperature for 2 h. Ten percent aqueous NH4Cl solutionwas added, followed by extraction with EtOAc. Theorganic layer was washed with water and brine, dried overanhydrous Na2SO4, filtered, and concentrated in vacuo. Theresidue was purified using silica gel column chromatography(11% EtOAc in hexane) to yield 9c (32.7 g, 56%) as a pale yellowoil.

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-(Benzyloxy)-3-bromobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yamamoto, Shuji; Shibata, Tsuyoshi; Abe, Kumi; Oda, Koji; Aoki, Takeshi; Kawakita, Yasunori; Kawamoto, Hiroshi; Chemical and Pharmaceutical Bulletin; vol. 64; 9; (2016); p. 1321 – 1337;,
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Adding a certain compound to certain chemical reactions, such as: 321-28-8, name is 1-Fluoro-2-methoxybenzene, belongs to ethers-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 321-28-8, Recommanded Product: 321-28-8

Step 1: Preparation of 3′-fluoro-4′-methoxy-acetophenone. Acetyl chloride (51.0 g, 0.65 mol) was added dropwise to a stirred solution of aluminum chloride (80.0 g, 0.6 mol) and chloroform (750 mL), maintaining the temperature between 5-10 C. The mixture was stirred for 10 minutes at 5 C before the dropwise addition of 2-fluoroanisole (62.6 g, 0.5 mol). The mixture was stirred at 0-10 C. for 1 hour and poured into ice (1 L). The resultant layers were separated and the aqueous layer was extracted with dichloromethane (2*250 mL). The combined organic layers were washed with water (2*150 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo to a volume of 300 mL. Hexanes were added and a white solid formed which was isolated by filtration and air dried. This material was recrystallized from a mixture of dichloromethane and hexanes to afford material suitable for use in the next step (77.2 g, 92%): mp 92-94 C.

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Reference:
Patent; G.D. Searle & Co.; US6407140; (2002); B1;,
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Related Products of 74137-36-3, 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. 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

Step 3: Pd(PPh3)4 (600 mg, 0.53 mmol, 0.1 eq.) and Cs2CO3 (3.40 g,10.52 mmol, 2.0 eq.) were added to a stirred solution of N-(5-(4,4,5,5- tetramethyl-1 ,3,2-d ioxaborolan-2-yl)-pyridi n-2-yl)-2-methylpyri midi ne-5-carboxamide (1 .78 g, 5.26 mmol, 1 .0 eq.) and dibromoanisole (1 .40 g, 5.26 mmol, 1.0 eq.) in dioxane (14 ml) at RT under a nitrogen atmosphere. The reaction mixture was heated to 100 ¡ãC for 16 h after which time it was allowed to cool to RT. The reaction mixture was then filtered and the filtrate was concentrated under reduced pressure. The residue was diluted withethyl acetate (100 mL) and washed with water and brine (100 mL each). The organic layer was dried over Na2504 and concentrated under reduced pressure to give crude product. This material was purified by flash chromatography (over silica gel 230-400 mesh) eluting with 2 percent methanol in DCM to afford pure N-[5-(3-bromo-5-methoxyphenyl)pyridin-2-yl]-2-methylpyrimidine-5-carboxamide (1.20 g; 57percent).

The chemical industry reduces the impact on the environment during synthesis 1,3-Dibromo-5-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; FROST BIOLOGIC, INC.; SIDDIQUI-JAIN, Adam; WO2015/127284; (2015); A2;,
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Reference of 702-24-9, These common heterocyclic compound, 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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.

Place ethyl 6,8-dichloroimidazo[ 1 ,2-bj pyridazine-3 -carboxylate (3 g, 11.54mmol), 1-(4-methoxyphenyl)-N-methylmethanamine (2.267 g, 15.00 mmol), and N,NDiisopropylethylamine (DIPEA) (4.03 mL, 23.07 mmol) in a 100 mL round bottle flask along with THF (15 mL). It was sealed and heated to 80¡ãC for 6 hours. The reactionmixture was concentrated and purified with silica gel chromatography. The product came out when eluting with 35percent ethyl acetate in hexane. The fractions containing product was collected and concentrated to provide the product (3.7 g, 9.87 mmol, 86percent yield, 100percentpurity). LC retention time 1.06 mm [Al. MS (ES+) m/z: 375 (MH). ?H NMR (400MHz, CHLOROFORM-d):8.14 – 8.09 (m, 1H), 7.20 – 7.13 (m, 2H), 6.89 – 6.83 (m, 2H), 6.11 (s, 1H), 5.49 (s, 2H),4.44 (q, J=7.2 Hz, 2H), 3.84 – 3.77 (m, 3H), 3.17 (s, 3H), 1.42 (t, J=7.2 Hz, 3H)

Statistics shows that 4-Methoxy-N-methylbenzylamine is playing an increasingly important role. we look forward to future research findings about 702-24-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WEINSTEIN, David S.; DUNCIA, John V.; SPERGEL, Steven H.; (76 pag.)WO2018/93968; (2018); A1;,
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Electric Literature of 10103-06-7,Some common heterocyclic compound, 10103-06-7, name is 2,3-Dimethoxynaphthalene, molecular formula is C12H12O2, 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.

(a) 2,3-Dimethoxy-naphthalene-1-carbaldehyde n-Butyl lithium in hexane (1.6 N, 31.3 ml) was gradually added to a solution of 2,3-dimethoxynaphthalene (9.4 g) and N,N,N’,N’-tetramethylethylenediamine (7.4 ml) in ether (150 ml) under argon at 0 C. The reaction mixture was stirred at room temperature for two hours, cooled to 0 C. and DMF (7.3 g) in ether (20 ml) added. The reaction mixture was stirred at room temperature overnight and poured in ice water. The product was extracted with ether, washed with water, dried, evaporated and recrystallized from ether. Yield: 4.2 g. 1H-NMR (DMSO-d6, 400 MHz): 10.68 (s,1H, CHO), 8.95-8.97 (m, 1H), 7.87-7.89 (m,1H), 7.80 (s,1H), 7.49-7.51 (m,2H), 4.00 (s,6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Dimethoxynaphthalene, its application will become more common.

Reference:
Patent; Baeckstroem, Reijo; Pystynen, Jarmo; Lotta, Timo; Ovaska, Martti; Taskinen, Jyrki; US2004/34011; (2004); A1;,
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Electric Literature of 6487-99-6, These common heterocyclic compound, 6487-99-6, name is 2-(3-Methylphenoxy)ethylamine, 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.

A solution of Example IB (25 mg, 0.08 mmol) in N,N-dimethylformamide (1.0 mL) was treated with a solution of 2-(3H-[l ,2,3]triazolo[4,5-]pyridin-3-yl)- l, 1 ,3,3- tetramethylisouronium hexafluorophosphate(V) (35 mg, 0.09 mmol) in N,N-dimethylformamide (0.5 mL). Then a solution of 2-(m-tolyloxy)ethanamine (12 mg, 0.08 mmol) in N,N- dimethylacetamide (0.15 mL) was added followed by N,N-diisopropylethylamine (0.037 mL, 0.21 mmol). The reaction was shaken at ambient temperature overnight and purified by HPLC (2-coupled C8 5 mupiiota 100 A columns 30 mm x 75 mm each, flow rate of 50 mL/minute, 5-90% gradient of acetonitrile in buffer (0.1 % trifluoroacetic acid in water)) to provide the title compound. JH NMR (400 MHz, DMSO-Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
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Electric Literature of 171290-52-1, 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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of the azide intermediate (0.1 mmol) in 0.2 mL of DMFin a microwave tube, CuSO4 (0.05 mmol) diluted in 50.0 muL of water,sodium ascorbate (0.025 mmol) and the alkyne (0.2 mmol) were added.The tube was sealed and the solution was irradiated (70 C, 150 W) for10 min and, then, TLC analysis showed the complete consumption ofthe starting material. The reaction was diluted with 15 mL of brine,extracted with ethyl acetate (3¡Á10 mL), dried by anhydrous Na2SO4and concentrated under reduced pressure. The resulting crude productwas purified by column chromatography on silica gel [hexane: ethylacetate, 60:40% (v/v)] yielding the expected product.

The chemical industry reduces the impact on the environment during synthesis 3,5-Dimethoxyphenylacetylene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zimmermann, Lara A.; de Moraes, Milene H.; da Rosa, Rafael; de Melo, Eduardo B.; Paula, Favero R.; Schenkel, Eloir P.; Steindel, Mario; Bernardes, Lilian S.C.; Bioorganic and Medicinal Chemistry; vol. 26; 17; (2018); p. 4850 – 4862;,
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Electric Literature of 10385-36-1, The chemical industry reduces the impact on the environment during synthesis 10385-36-1, name is 1-Bromo-2,3,4-trimethoxybenzene, I believe this compound will play a more active role in future production and life.

EXAMPLE 10 1-(2,3,4-Trimethoxyphenyl)-2,2,4,4-tetramethyl-3-(4-phenylpiperazinyl)-cyclobutanol-(1) Prepared from 2,2,4,4-tetramethyl-3-(4-phenyl-piperazinyl)-cyclobutanone by Grignard reaction with 2,3,4-trimethoxy-bromobenzene in tetrahydrofuran. Yield: 14% of theory; m.p. of the cis-compound: 148-150C (from ethyl acetate).

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-2,3,4-trimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim GmbH; US3931185; (1976); A;,
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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. 456-49-5, name is 1-Fluoro-3-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Fluoro-3-methoxybenzene

The 3-fluoro anisole (15 g, 119 mmol) was placed in THF (300 mL) and cooled to about -78 C., and then n-BuLi (89 mL 1.6 M in hexanes) was added while maintaining the temperature at around -70 C. The mixture was stirred for about 15 minutes, and bromine (18.9 g, 119 mmol) was added over 10 minutes. The mixture was warmed to r.t. and stirred overnight. The mixture was quenched with water, diluted with ether (500 mL) and partitioned between water/ether (1/1 300 mL). The water layer was back extracted with ether (250 mL), and the combined organic fractions were dried, filtered and concentrated. The dark residue was distilled under house vacuum (product 115-130 C.) to recover about 13.8 g of the product as a gray oil (57%/).

According to the analysis of related databases, 456-49-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Briner, Karin; Doecke, Christopher William; Mancuso, Vincent; Martinelli, Michael John; Richardson, Timothy Ivo; Rothhaar, Roger Ryan; Shi, Qing; Xie, Chaoyu; US2004/82590; (2004); A1;,
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