Category: 53087-13-1

Electric Literature of 53087-13-1,Some common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, molecular formula is C13H11BrO, 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.

Iodine, warmed up with magnesium, was added to a suspension of magnesium tunings (i .29 g,52.8 mmol) in dry THF (50 mL). The mixture was ref luxed and about 5% of a solution of 3-bromophenol (i3.9 g, 52.8 mmol) was added. When the reaction had started, the solution of the bromide was added drop-wise and the mixture was then ref luxed for one more hour. Themixture was cooled down to about 5 00 and a solution of the cyclopentanone (4.44 g, 52.8 mmol) in THF (50 mL) was added drop-wise. The mixture was stirred at rt for 72 h, then the reactio was quenched with cooled saturated ammonium chloride solution and extracted with diethyl ether (x3). The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The product was purified by silica gel chromatography (isohexane / EtOAc),which gave the title compound (8.5 g, 54%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(Benzyloxy)-3-bromobenzene, its application will become more common.

Reference:
Patent; MEDIVIR AB; KALAYANOV, Genadiy; TORSSELL, Staffan; WAeHLING, Horst; WO2015/34420; (2015); 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. 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, A new synthetic method of this compound is introduced below., SDS of cas: 53087-13-1

A solution of 1-(benzyloxy)-3-bromobenzene (for a preparation see Intermediate 21 , 263 mg, 1.0 mmol) in 1 ,4-dioxane (8 mL) was added to a mixture of £>/s(pinacolato)diboron (1 .27 g, 5.0 mmol), potassium acetate (392 mg, 4.0 mmol) and [1 ,1 – t)/’s(diphenylphosphino)ferrocene]dichloropalladium(ll), (PdCI2(dppf)) (37 mg, 5 mol%). The reaction mixture was heated in a microwave at 1 10C for 60 minutes. The cooled reaction mixture was diluted with ethyl acetate (20 mL) and filtered through Celite. The filtrate was dried and evaporated to give 2-(3-(benzyloxy)phenyl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (310 mg, 1.000 mmol, 100 in the next step without further

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; BAMBOROUGH, Paul; BARKER, Michael David; BIT, Rino Antonio; BROWN, John Alexander; CAMPBELL, Matthew; GARTON, Neil Stuart; LINDON, Matthew J; SHIPLEY, Tracy Jane; THEODOULOU, Natalie Hope; WELLAWAY, Christopher Roland; WESTAWAY, Susan Marie; WO2014/140077; (2014); A1;,
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Electric Literature of 53087-13-1, These common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, 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.

Magnesium (172.4 mg; made by Wako Pure Chemical Industries Co., Ltd.), dehydrated THF (5 mL), dibromoethane (20 muL; made by Tokyo Chemical Industry Co., Ltd.), and 1-(benzyloxy)-3-bromobenzene-THF solution [15 mL; solution prepared by dissolving 1-(benzyloxy)-3-bromobenzene (1.3146 g; made by Tokyo Chemical Industry Co., Ltd.) in dehydrated THF (15 mL)] were added and stirred for one hour by reflux in a nitrogen atmosphere. The reaction solution was cooled to – 78C and bubbled for 20 minutes by SO2 gas. The reaction solution was brought to room temperature, bubbled for 10 minutes with nitrogen gas, and filtered. The filtrate was concentrated, and the residue obtained was dissolved in CH2Cl2 (25 mL), then cooled to 0C. SO2Cl2 (0.6 mL; made by Wako Pure Chemical Industries Co., Ltd.) was added to this solution and stirred overnight while warming to room temperature. Water was added to the reaction solution. After filtering by Celite, the filtrate was washed with brine. The organic layer was dried by anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The title compound was obtained as a crude product (1.3811 g). This crude product was used in the next reaction without any particular purification.

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asahi Kasei Pharma Corporation; EP2484668; (2012); A1;,
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Electric Literature of 53087-13-1, 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. 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a 30 mL flamed-dried flask equipped with stir bar and a nitrogen-filled balloon were added 2,2,6,6-tetramethylpiperidine (1.2 equiv) and THF (12 mL). After cooled to 0 C with an ice waterbath, n-BuLi (2.5 M in hexane, 1.2 equiv) was added dropwise and the reaction was stirred at 0 C for 0.5 h. To a 100 mL flame-dried flask equipped with a stir bar and a nitrogen-filled balloon were added THF (30 mL), benzyne precursor (1 equiv), and corresponding ketene silyl acetals9 (1.5 equiv) and was cooled to 78 C with an acetone-dry ice bath before in situ generated lithium tetramethylpiperidine was added dropwise. The reaction was monitored and aqueous NH4Cl was added upon disappearance of the benzyne precursor. After warming to rt, the reaction mixture was extracted with ethyl acetate (30 mLx3), washed with brine, and concentrated under reduced pressure. Acetonitrile (30 mL) was added to the concentrated reaction system and cooled to 0 C with an ice-water bath followed by slow addition of hydrofluoric acid (27.6 M, 10 equiv). Upon completion, the reaction was heated to 40 C overnight before water (100 mL) was added. The mixture was extracted with ethyl acetate (30 mLx3), washed with brine, and dried with Na2SO4. The combined organic extract was concentrated under reduced pressure and purified by column chromatography on silica gel to afford the following compounds. 4.6.2. 8-Ethyl-5-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-one (10). Compound 10 was obtained as colorless oil (876 mg) from 6a and tert-butyl((1-methoxybut-1-en-1-yl)oxy)dimethylsilane in 62% yield, Rf=0.8 (Hexane/EtOAc=5:1); 1H NMR (400 MHz, CDCl3) delta 7.40 (dd, J8.4, 7.1 Hz, 1H), 6.99 (d, J7.1 Hz, 1H), 6.78 (d, J8.4 Hz,1H), 4.13-4.06 (m, 4H), 1.98-1.72 (m, 2H), 1.04 (t, J7.5 Hz, 3H). 13C NMR (101 MHz, CDCl3) delta 188.9 (s), 156.0 (s), 153.5 (s), 137.5 (s), 131.1(s), 116.0 (s), 114.6 (s), 65.0 (s), 59.7 (s), 23.3 (s), 11.5 (s). IR: gamma 2963, 2934, 2876, 2359, 2340, 1766, 1602, 1574, 1482, 1455, 1435, 1277, 1157, 1123, 1020, 941, 799 cm-1. HRMS calcd for C16H14NaO2[MNa]: 261.0886, found: 261.0879.

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; Chen; Savage, Nikolas A.; Dong, Guangbin; Tetrahedron; vol. 70; 27-28; (2014); p. 4135 – 4146;,
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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. 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C13H11BrO

A stirred mixture of 1-benzyloxy-3-bromo-benzene (10.56 g, 40.1 mmol) and dry THF (35 mL) was cooled to -78 C., evacuated and refilled with nitrogen for 10 cycles. To this clear solution was slowly added n-butyllithium (17.7 mL, 44.1 mmol) and stirred for 20 min. Then a mixture of 3,5-dimethoxy-benzaldehyde (7.34 g, 44.1 mmol) in dry THF (30 mL) was added and stirred for 1 hour at -78 C. The mixture was quenched with isopropanol (18.5 mL, 241 mmol) and added water (30 mL). The mixture was extracted with EtOAc (3*80 mL). The combined organic phases were washed with water (2*80 mL), dried over MgSO4 and concentrated to oil, which was purified by flash column chromatography (EtOAc/Hexane) to give (3-benzyloxy-phenyl)-(3,5-dimethoxy-phenyl)-methanol as an oil (11.54 g, 82% yield): 1H NMR (CDCl3) delta 2.21 (d, J=4 Hz, 1H, OH), 3.76 (s, 6H, 2OCH3), 5.04 (s, 2H, CH2), 5.72 (d, J=4 Hz, 1H, CH), 6.36 (t, J=2 Hz, 1H, Ar), 6.54 (d, J=2 Hz, 2H, Ar), 6.85-7.04 (m, 3H, Ar), 7.21-7.43 (m, 6H, Ar).

According to the analysis of related databases, 53087-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Celgene Corporation; US2005/107339; (2005); A1;,
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Related Products of 53087-13-1, 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. 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 1-benzyloxy-2-bromobenzene (12.8 g, 48.7 mmol) and n-butyllithium (55 mmol) in THF (150 mL) was stirred for 20 min at -78 C, treated with tri-iso-propyl borate (34 mL, 147 mmol), stirred for 20 minutes at -78 C, then 30 minutes at ambient temperature. The mixture was reduced in volume by rotary evaporation, diluted with ethyl acetate washed sequentially with 1M HCl (twice), water, and brine, dried (MgSO4) and concentrated to provide a white solid which was triturated with hexanes to provide the title compound as a white powder (7.04 g). MS (DCI/NH3) m/e 246 (M+NH4)+.

The chemical industry reduces the impact on the environment during synthesis 1-(Benzyloxy)-3-bromobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ABBOTT LABORATORIES; EP1080070; (2006); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, 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 53087-13-1, SDS of cas: 53087-13-1

Iodine, warmed up with magnesium, was added to a suspension of magnesium tunings (1.29 g, 52.8 mmcl) in dry THF (50 mL). The mixture was refluxed and about 5% of a solution of 3- bromophenol (13.9 g, 52.8 mmcl) was added. When the reaction had started, the solution of thebromide was added drop-wise and the mixture was then refluxed for one more hour. The mixture was cooled down to about 5 C and a solution of the cyclopentanone (4.44 g, 52.8 mmcl) in THF (50 mL) was added drop-wise. The mixture was stirred at rt for 72 h, then the reactio was quenched with cooled saturated ammonium chloride solution and extracted with diethyl ether (x3). The organic phase was washed with brine, dried (Na2SO4), filtered andconcentrated. The product was purified by silica gel chromatography (isohexane / EtOAc), which gave the title compound (8.5 g, 54%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(Benzyloxy)-3-bromobenzene, and friends who are interested can also refer to it.

Reference:
Patent; MEDIVIR AB; KALAYANOV, Genadiy; PINHO, Pedro; WESTERLIND, Hans; WIKTELIUS, Daniel; WAeHLING, Horst; WO2015/56213; (2015); A1;,
Ether – Wikipedia,
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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. 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, A new synthetic method of this compound is introduced below., Quality Control of 1-(Benzyloxy)-3-bromobenzene

Compound 2: A flask charged with compound 1 (2818 g, 10.71 mol), (3- fluorophenyl)boronic acid (1574 g, 11.25 mol), and Na2C03 (1135.1 g, 10.71 mol, 1 equiv) was evacuated and refilled with Ar for three times. Deionized water (5.6 L), DME (14 L) and Pd(PPh3)4 (123.8 g, 0.107 mol) were added sequentially. The resulting mixture was degassed and refilled with Ar for three times and then refluxed for 7 h. The suspension was filtered through Celite (500 g) plug. The filtrate was a two-phase mixture. The organic phase was separated. The aqueous phase was extracted with EtOAc (10 L). The combined organic extracts was dried over Na2S04 (3 kg), filtered and concentrated. Half of the crude product was purified by column chromatography (silica gel, eluting with 20% CH2Cl2 in hexanes) to give compound 2 (1040 g, 70% yield) as a white solid.

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REATA PHARMACEUTICALS, INC.; JIANG, Xin; VISNICK, Melean; BENDER, Christopher, F.; BOLTON, Gary; CAPRATHE, Bradley; LEE, Chitase; (393 pag.)WO2019/222269; (2019); 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. 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C13H11BrO

A degassed mixture of 3-benzyloxy-phenyl bromide (28) (0.176 g, 0.67 mmol), 3- methoxycarbonylphenylboronic acid (0.18 g, 1 mmol), barium hydroxide (0.25 g, 1.47 mmol), Pd(PPh3)4 (0.077 g, 0.067 mmol), DME (5 mL) and H2O (3 mL) was microwaved with vigorous stirring using a CEM-discover system (ram time: 2min, hold time: 5min, temperature: 120C, pressure: 200 psi, power: 250 W). The crude reaction mixture filtered through a plug of celite and concentrated in vacuo. The residue obtained was purified by flash column chromatography (25% diethyl ether-hexane) to give the title compound (29) (0.118 g, 60% yield) as a viscous liquid.[0280] 29 was confirmed as follows: 1H NMR (500 MHz, CDCl3) delta 8.27 (t, J = 1.5 Hz, 1H), 8.20 (dd, J = 8.0 Hz, J = 1.5 Hz, 1H), 7.76 (dd, J = 8.0 Hz, J = 2.0 Hz, 1H), 7.50 (t, J = 8.0 Hz, 1H), 7.47 (d, J = 7.5 Hz, 2H), 7.42-7.32 (m, 4H), 7.25-7.22 (m, 2H), 7.00 (dd, J = 8.2 Hz, J = 2.0 Hz, 1H), 5.13 (s, 2H), 3.95 (s, 3H).

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHEASTERN UNIVERSITY; WO2009/52319; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 53087-13-1,Some common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, molecular formula is C13H11BrO, 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.

Reference Example 4 1-(3,4,5,6-Tetramethoxy-2-methylphenyl)-1-(3- benzyloxyphenyl) methanol An anhydrous tetrahydrofuran (50 ml) solution of 3,4,5,6-tetramethoxy-2-methylbenzaldehyde (14 g, 0.058 mol) was added dropwise under ice cooling to a Grignard reagent (150 ml tetrahydrofuran solution) prepared from 3-(benzyloxy)bromobenzene (18.4 g, 0.070 mol) and magnesium (1.87 g, 0.077 mol), and the resulting solution was stirred for 2 hours. The reaction solution was poured in an aqueous solution of saturated ammonium chloride and extracted with ether. The extract was washed with saturated brine and then dried. The reaction solution was filtered, the filtrate was concentrated and the obtained crude product was purified by silica gel column chromatography (hexane: ethyl acetate = 4:1) to obtain the titled compound (23.5 g, 0.055 mol, 95%).

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Suntory Pharma Co., Ltd.; Daiichi Suntory Biomedical Research Limited; EP1314712; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem