Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 446-59-3, name is 2-Bromo-1-fluoro-3-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 446-59-3, COA of Formula: C7H6BrFO

A flame dried round bottle (evacuated under vacuum and filled with N2 ) was fitted with mechanical stirring, and charged with tert-butyl (S)-4-(6-chloro-8- fluoroquinazolin-4-yl)-3-methylpiperazine-1-carboxylate (685 mg, 1.80 mmol, 1.0 eq.) solution in dry THF. Bis(2,2,6,6-tetramethylpiperidinyl)zinc, lithium chloride, magnesium chloride complex ((TMP)2Zn?2 MgCl2?2 LiCl) (0.35 M solution in THF/toluene, 1.0 eq. ) was dropwise added. The reaction was allowed to stir for 45 min at RT and then degassed by bubbling nitrogen through the solution for 15 min. Solid 2- bromo-1-fluoro-3-methoxybenzene (1.0 eq.) and CPhos 3rd generation precatalyst (0.1 eq.) were added, and the resulting mixture was stirred at 40 C for 16 h. The reaction mixture was concentrated in vacuo, dissolved in ethyl acetate, cooled in an ice bath, and quenched with a 1:1 solution of saturated ammonium chloride and H2O. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (stepwise gradient of 20%-30% EtOAc in hexanes) to afford the desired product (504 mg, 56% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1-fluoro-3-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; ARAXES PHARMA LLC; LI, Liansheng; FENG, Jun; LONG, Yun Oliver; LIU, Yuan; WU, Tao; REN, Pingda; LIU, Yi; (335 pag.)WO2016/164675; (2016); A1;,
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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. 10541-78-3, name is 2-Methoxy-N-methylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 2-Methoxy-N-methylaniline

EXAMPLE VI Preparation of N’-(4-Ethoxycarbonylphenyl)-N-(2-methoxyphenyl)-N-methylformamidine A mixture of ethyl N-(4-ethoxycarbonylphenyl)formimidate (Example Ia) (4.9 g, 0.022 mol) and 2-methoxy-N-methylaniline (3.2 g, 0.022 mol) were heated at 180 until 1.3 ml of ethanol had been collected by distillation. The resulting yellow oil was flash distilled to yield the desired product, bp~200 C. (0.05 mm).

The synthetic route of 10541-78-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Givaudan Corporation; US4021471; (1977); A;,
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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. 588-96-5, name is p-Bromophenetole, A new synthetic method of this compound is introduced below., Quality Control of p-Bromophenetole

General procedure: CS127 was prepared using a modified literature procedure [16]. A solution of butyllithium (1. hexane, 0.15 mL) was added to a solution of 4-bromotoluene (8.52 mg, 0.050 mmol) in hexane (15 mL). After stirring for 1 h, N,N’-diisopropylcarbodiimide (6.29 mg, 0.050 mmol) was added dropwise. The solution was stirred for 1 h at room temperature and then the dimer [(FMeppy)2Ir(mu-Cl)]2 (30 mg, 0.025 mmol) was added. The mixture was heated overnight at 70 C. After being cooled to room temperature, the resulting precipitate was collected and washed with diethyl ether. The dried product was obtained as a yellow powder. Yield 65%.

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:
Article; Sahin, Cigdem; Goren, Aysen; Varlikli, Canan; Journal of Organometallic Chemistry; vol. 772; (2014); p. 68 – 78;,
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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. 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

b) 52.0 g (186 mmol) 1-Bromo-4-(2-bromoethoxy)benzene are added to 300 mL THF and cooled to 0 C. Within 30 min 25.0 g (223 mmol) KOtBu are added to this mixture in several portions. Cooling is removed and the reaction mixture is stirred at rt over night. The reaction is quenched by the addition of water. The resulting mixture is extracted with EtOAc (2×). The organic phases are combined, washed with brine, dried over MgSO4 and the solvent is removed in vacuo. The resulting product is used without further purification.

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; ROTH, Gerald Juergen; FLECK, Martin; LEHMANN-LINTZ, Thorsten; NOSSE, Bernd; US2013/143876; (2013); A1;,
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Related Products of 105404-89-5, 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. 105404-89-5, name is 2,7-Dibromo-3,6-dimethoxynaphthalene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

0.125 mol, 43.4 g of [Intermediate 1-1] and 0.301 mol of (4-chloro-2-fluorophenyl) boronic acid at room temperature,52.5g and 0.815mol of Ce2CO3, 266g and 11.6g of TTP (tetrakis (triphenylphosphine) palladium (0)) were added together with 500mL of 1,4-dioxane and refluxed.After 4 hours, the reaction was cooled to room temperature, 500 ml of H 2 O was added, and extracted with EA. After filtration, the obtained solid was recrystallized from EA (ethyl acetate) and Hx (normal hexane) to obtain 0.09 mol of [Intermediate 1-2] and 41.0 g (yield 73%).

The synthetic route of 2,7-Dibromo-3,6-dimethoxynaphthalene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; Gu Gi-dong; Yoon Jeong-min; Keum Su-jeong; Kim Myeong-gon; (62 pag.)KR2019/111687; (2019); A;,
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Reference of 2525-16-8, These common heterocyclic compound, 2525-16-8, name is 7-Methoxy-3,4,5,6-tetrahydro-2H-azepine, 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 ethyl N-[3-(3-amidinophenyl)-2-(E)-propenyl]-N-[3-methyl-4-(piperidin-4-yloxy)phenyl]sulfamoylacetate (640 mg) obtained in example 65(a) in ethanol (12 ml) were added successively 7-methoxy-3,4,5,6-tetrahydro-2H-azepine (348 mg) and triethylamine (0.26 ml) at room temperature and the resulting mixture was stirred at room temperature for 2.5 days and then evaporated in vacuo.. The residue obtained was purified by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: 20 % acetonitrile/water).. Subsequently, to a solution of the amorphous solid obtained in ethanol (5 ml) was added a 4N solution of hydrogen chloride in dioxane (0.42 ml), and the resulting mixture was evaporated to dryness in vacuo.. The residue obtained was dissolved in water and then lyophilized to afford the title compound (336 mg, yield: 40 %) as a colorless amorphous solid. 1H NMR (400MHz, DMSO-d6) delta ppm: 1.23 (3H, t, J=7.0), 1.52-1.64 (4H, m), 1.68-1.82 (4H, m), 1.98-2.09 (2H, m), 2.17 (3H, s), 2.87 (2H, m), 3.48 (2H, m), 3.65-3.75 (2H, m), 3.77-3.88 (2H, m), 4.19 (2H, q, J=7.0), 4.33 (2H, s), 4.44 (2H, d, J=6.0), 4.74 (1H, m), 6.44 (1H, dt, J=16.0, 6.0), 6.57 (1H, d, J=16.0), 7.06 (1H, d, J=8.5), 7.25 (1H, dd, J=8.5, 2.5), 7.28 (1H, d, J=2.5), 7.55 (1H, t, J=8.0), 7.69 (1H, d, J=8.0), 7.72 (1H, d, J=8.0), 7.89 (1H, s); IR (KBr, cm-1): 1738, 1675, 1628, 1351, 1157.

Statistics shows that 7-Methoxy-3,4,5,6-tetrahydro-2H-azepine is playing an increasingly important role. we look forward to future research findings about 2525-16-8.

Reference:
Patent; Sankyo Company, Limited; EP1375482; (2004); A1;,
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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. 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-6-methoxynaphthalene

Under argon atmosphere, 2.37 g (0.01 mol) of 2-bromo-6-methoxynaphthalene and 40.578 g of Pd (PPh3)(0.5 mmol) of CuI, 0.095 g (0.5 mmol) of CuI and 30.131 g (0.5 mmol) of PPh. After the addition was completed, the mixture was purged with argon three times,Air was removed from the reaction flask, and then 15 ml of triethylamine, 1.96 ml of trimethylethynylsilane and 30 ml of tetrahydrofuran were added.After the addition was completed, the system was allowed to rise to 78 C for 20 h.The reaction mixture was filtered to remove a large amount of insoluble salts and solids. To the filtrate was added 150 ml of methylene chloride and the mixture was washed three times with 150 ml of 5% diluted hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. Ether to do the agent.After the column liquid was swirled to a white solid precipitation stopped rotating when placed at room temperature precipitated a large number of white solid, filtered and dried to give a white solid6-Methoxy-2-naphthylethynyltrimethylsilyl2.50 g, yield 98.4%

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; East China University of Science and Technology; Shen Dong; Liu Haipeng; Zheng Zhigang; (18 pag.)CN106336350; (2017); A;,
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Some common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, molecular formula is C8H9BrO2, 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. category: ethers-buliding-blocks

General procedure: General procedure for the preparation of arylalkynes 2a-q (non-decarboxylative approach, method A). An oven-dried 20 mL Schlenk tube equipped with a magnetic stirring bar and a rubber septum was charged with Pd(OAc)2 (6.7 mg, 30 mumol), tri(p-tolyl)phosphine (18.2 mg, 60 mumol). After purging the vessel with alternating vacuum and nitrogen cycles, degassed THF (3 mL), 1,8-diazabicycloundec-7-ene (450 muL, 3.0 mmol), 2-methylbut-3-yn-2-ol (120 muL, 1.24 mmol) and aryl bromides 1a-q (1.0 mmol) were added via a syringe (solid aryl bromides were added as solution in degassed THF) and the mixture was stirred at 80 C for 6 h. After cooling to rt the mixture was diluted with water (20 mL) and extracted with AcOEt (3 20 mL). Combined organic extracts were washed with H2O (20 mL), saturated aqueous NaCl (20 mL), dried over MgSO4 and concentrated in vacuum. The crude product was purified by silica gel chromatography (eluant hexane/Et2O gradient) affording the corresponding products 2a-q.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20469-65-2, its application will become more common.

Reference:
Article; Caporale, Andrea; Tartaggia, Stefano; Castellin, Andrea; De Lucchi, Ottorino; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 384 – 393;,
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Adding a certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, 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 1535-73-5, Computed Properties of C7H6F3NO

[00310] A reaction vial was charged with 2-benzyl-5-chloro-l,2,3,4-tetrahydro-2,6-naphthyridine(25.00 mg, 0.09662 mmol), 3-(trifluoromethoxy)aniline (42.8 mg, 0.000242 mol), tris(dibenzylideneacetone)dipalladium(0) (2.2 mg, 0.0000024 mol), xantphos (3 mg, 0.000005 mol), sodium tert-butoxide (14 mg, 0.00014 mol), and toluene (0.500 mL, 0.00469 mol) and tert-butyl alcohol (0.1 mL, 0.001 mol) and the vial was flushed with argon. The reaction mixture was then stirred at 110 0C in a microwave for 30 minutes. The reaction mixture was then filtered and solvent removed and the residue purified by prep HPLC to get the pure compound as a yellow solid. MS (M+H)= 400.4;1H-NMR (CDCl3): (400 MHz) 88.03 (d, 7=4.66 Hz, IH), 7.61 (bs, lH),7.48-7.44 (m, 2H), 7.40-7.28 (m, 5H), 6.83 (d, J=7.98 Hz, IH), 6.51 (d, 7=5.1 1 Hz, IH), 6.25 (bs, IH), 3.85 (s, 2H), 3.70 (s, 2H), 3.00 (t, J=5.50 Hz, 2H), 2.76 (t, 7=5.50 Hz, 2H)

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, 3-Trifluoromethoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RENOVIS, INC.; WO2009/11904; (2009); A1;,
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Application of 1663-61-2,Some common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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: To asolution of hydrazide (0.73 mmol) in 10 mL of anhydrous ethanol, added triethyl orthoester (0.81 mmol) and ammonium chloride (0.219 mmol). The solution was stirred and heated to reflux until it complete (0.5-18 h). The reaction mass was cooled to room temperature and concentrated under vacuum. The crude product was made into slurry in a mixture of hexanes and ether (3:1), filtered,washed with deionized water or purified by column chromatography.

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gnanasekaran, Krishna Kumar; Nammalwar, Baskar; Murie, Maeghan; Bunce, Richard A.; Tetrahedron Letters; vol. 55; 50; (2014); p. 6776 – 6778;,
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