Category: 53087-13-1

Application 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.

2) 1-benzyloxy-3-bromobenzene (2) undergoes Gridnard reaction to prepare 3-benzyloxyphenyl magnesium bromide, 3-benzyloxyphenyl magnesium bromide undergoes esterification, hydrolysis reaction to prepare the compound 3-benzyloxybenzeneboronic acid (3)In a 250mL two-necked flask add a clean magnesium ribbon 2.18g (90mmol), three grain-doses of iodine. Under nitrogen protection, add 1-benzyloxy-3-bromobenzene (2) 15.79g (60mmol) in dry tetrahydrofuran 40mL, the reaction was heated at reflux for 5 hours to obtain a Grignard reagent 3-benzyloxyphenyl magnesium bromide. The above-described dry tetrahydrofuran was cooled to room temperature, at minus 20 degrees Celsius was added dropwise trimethyl borate 9.36g (90mmol) in dry tetrahydrofuran solution. After addition, 3 hours reaction at room temperature. Then, 100mL saturated aqueous ammonium chloride was added and then hydrolysis reaction overnight. After reaction was complete, recover tetrahydrofuran under reduced pressure, and then acetic acid was added 100mL extraction with ethyl acetate, the organic phasewas washed with water and saturated sodium chloride solution and finally organic phase was dried over anhydrous sodium sulfate and the solvent evaporatedunder reduced pressure to give a white 3-benzyloxybenzene boronic acid (3)7.53g of crude product, yield 55%.

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

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, Safety of 1-(Benzyloxy)-3-bromobenzene

526 mg (2.0 mmol) of 1-(benzyloxy)-3-bromobenzene, 209 mul (2.4 mmol) of morpholine, 283 mg (2.8 mmol) of sodium t-butoxide, 9 mg (0.005 mmol) of tris(dibenzylidine acetone)dipalladium (O) 19 mg (0.015 mmol) of (No.)-BINAP were placed in a flask, 5 ml of toluene was added thereto, and the mixture was stirred at 80C for 20 hours. The reaction mixture was cooled to room temperature, 20 ml of ethyl acetate was added thereto, and filtered through Cellite. The resulting filtrate was concentrated under a reduced pressure, and the residue was subjected to column chromatography using 30% ethyl acetate/hexane as an eluent to obtain 430 mg (yield 80%) of 4- (3-(benzyloxy)phenyl)morpholine.

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:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; OSCOTEC INC.; WO2005/123054; (2005); A1;,
Ether – Wikipedia,
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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. Application In Synthesis of 1-(Benzyloxy)-3-bromobenzene

Magnesium strip (1.29 g, 52.8 mmol) in anhydrous THF (50 mL)To the suspension was added iodine which was heated with magnesium.The mixture was refluxed and an approximately 5% solution of 3-bromobenzyl phenol(13.9 g, 52.8 mmol) was added.At the beginning of the reaction, the bromide solution is added dropwise and the mixture is then refluxed again1 hour. The mixture was cooled to about 5 C and a solution of cyclopentanone (4.44 g, 52.8 mmol) in THF (50 mL) was added dropwise. The mixture was stirred at rt for 72 h,The reaction was then quenched with a 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%).

The synthetic route of 1-(Benzyloxy)-3-bromobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVIR AB; KALAYANOV, GENADIY; TORSSEL, STAFFAN; WAHLING, HORST; (130 pag.)TW2018/15396; (2018); A;,
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Synthetic Route 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.

Step 1: Methyl 2-(3-(benzyloxy)phenyl)-2-hydroxy-2-phenylacetate Magnesium turnings (40.9 g, 1.71 mol) were placed in the three necked round bottom flask under argon. Anhydrous THF (1800 mL) and crystals of iodine (6.18 g, 0.024 mol) were added then 1-(benzyloxy)-3-bromobenzene (384.69 g, 1.46 mol) was added in portions. The internal temperature rose to 60 C. and the reaction foamed. The reaction was stirred for 2.5 hours at reflux. In another flask, a solution of methyl benzylformate (200.00 g, 1.22 mol) in anhydrous THF (2000 mL) was cooled to -70 C. under argon and to this the Grignard reagent was added dropwise over 3 hours. The reaction was allowed to slowly warm to room temperature and stirred at this temperature for 18 hours. The reaction was quenched with ammonium chloride solution. Layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic fractions were washed with brine and dried over anhydrous magnesium sulfate. The filtrate was evaporated at reduced pressure to afford an oil. The resultant oil was evaporated with hexane twice to afford a solid (473.15 g). The solid was refluxed with 4730 ml hexane (10 ml/g) for 5 min, then allowed to cool to room temperature and stirred for 1 hour, then filtered and washed with hexane to obtain 386.34 g (HPLC: 83.85%). The product was crystallized in 3930 ml iPrOH (13 ml/g). The mixture was milky at reflux, was filtered (solid: 5.85 g, HPLC: 95.95%) and the filtrate was allowed to crystallized for 18 hours. The resulting precipitate was stirred for 1.5 hour at 10 C., then filtered and washed with hexane to afford the title product (180.54 g, 42%). 1H NMR (400 MHz, DMSO-d6); delta 7.44-7.22 (m, 11H), 6.98-6.93 (m, 2H), 6.92-6.88 (m, 1H), 6.68 (s, 1H, OH), 5.05 (s, 2H), 3.70 (s, 3H).

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

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; RANCATI, Fabio; Rizzi, Andrea; Carzaniga, Laura; Linney, Ian; Knight, Chris; Schmidt, Wolfgang; (120 pag.)US2018/16267; (2018); A1;,
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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., name: 1-(Benzyloxy)-3-bromobenzene

To a solution of 1-(benzyloxy)-3-bromobenzene (1.00 g) in 1,2-dimethoxyethane (15 mL) were added tris(dibenzylideneacetone)dipalladium(0) (180 mg), 2′-[dicyclohexylphosphino]-N,N-dimethylbiphenyl-2-amine (150 mg), piperidine (500 muL), and tripotassium phosphate (2.5 g) at room temperature, and the mixture was stirred at 110C for 21 hours. After the reaction mixture was cooled to room temperature, insolubles were separated by filtration and the solvent was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0 – 85/15) to obtain 1-[3-(benzyloxy)phenyl]piperidine (722 mg).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 53087-13-1.

Reference:
Patent; Astellas Pharma Inc.; EP2194044; (2010); A1;,
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, HPLC of Formula: C13H11BrO

Example 66; 2-[4-[2-[5-[2-[2-benzyloxy-4-[butyl(4-hydroxybutyl)amino]phenyl]vinyl]thiophene-2-yl]vinyl]-3-cyano-5,5-dimethyl-2(5H)-furanylidene]propanedinitrile(66-1) 4-[(3-benzyloxyphenyl)butylamino]-1-butanol In 75 ml of dioxane were dissolved 5.19 g (19.7 mmol) of 3-benzyloxybromobenzene and 3.72 g (25.6 mmol) of 4-butylamino-1-butanol. To this mixture was added 5.89 g (29.5 mmol) of potassium hexamethyldisilazide and the mixture was stirred with heating at 100 C. for 22 hours. After the reaction mixture was poured into 200 ml of water, extraction with chloroform, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography to give 2.22 g of a light brown oily matter (yield: 34.4%). 1H-NMR (600 MHz, CDCl3) delta: 0.93 (3H, t, J=7.7 Hz), 1.29-1.35 (2H, m), 1.51-1.66 (6H, m), 3.22 (2H, t, J=7.7 Hz), 3.26 (2H, t, J=7.7 Hz), 3.66 (2H, t, J=6.9 Hz), 5.05 (2H, s), 6.27-6.31 (3H, m), 7.11 (1H, t, J=8.2 Hz), 7.30-7.33 (1H, m), 7.37-7.39 (2H, m), 7.43-7.45 (2H, m)

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:
Patent; Otomo, Akira; Aoki, Isao; Miki, Hideki; Tazawa, Hidehisa; Yokoyama, Shiyoshi; US2012/172599; (2012); 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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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. HPLC of Formula: C13H11BrO

.2 eq BuLi in hexane,1.2 eq TMEDA, 8 eq SO2 in Et2O, 3 eq N-chlorosuccinimide, EtjO, -75 C to 25 C, then dioxane, aq NH3. 250C1 16 hA solution of l-benzyloxy-3-bromobenzene (28.3 g) in Et2O (375 mL) is cooled to – 70 C and treated with TMEDA (19.2 mL) and tt-BuLi in hexane (1.6 M, 79 mL). The solution is stirred at -70 C for 1 h and transferred into a cooled solution (-70 0C) of SO2 (54.4 g) in Et2O (375 mL). The mixture is kept at -700C for 15 minutes, then allowed to warm to RT over 1 h. The solvent is evaporated and the residue is suspended in aqueous sodium phosphate (IM, 750 mL, pH 6). EtOAc (500 mL) is added and the solution is cooled to 00C. JV-Chlorosuccinimide (43.5 g) is slowly added and the pH is readjusted to pH 6 by addition OfNa3PO4. The reaction mixture is stirred vigorously for 1 h. The phases are separated and the aqueous phase is extracted twice with EtOAc. The combined organic phases are washed with H2O and brine, dried and concentrated to give a yellowish oil. The residue is taken up in dioxane (400 mL) and NH3 in H2O (28%, 200 mL) is added. The reaction mixture is stirred for 12 h and then concentrated to dryness. The residue is chromatographed on SiO2 gel (eluent hexanes/EtOAc 4:1 to 3:7) to give 3-benzyloxy- benzenesulfonamide as a white powder. API-MS: M-I ?= 262.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 53087-13-1, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; WO2007/120595; (2007); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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., Computed Properties of C13H11BrO

Benzylation of 3-bromophenol 1 with benzyl chloride and potassium carbonate in DMF affords compound 2. Palladium (0)-catalyzed cross-coupling reaction of 2 with bis(pinacolato)diboron, PdCl2(dppf), and potassium carbonate in DMSO at 80 C. gives rise to compound 3 (Ishiyama, T; Murata, M; Miyaura, N. J. Org. Chem. 1995, 60, 7508). Debenzylation of 3 with Pd/C at 60 psi hydrogen in MeOH produces the target compound 4 (Pennington, T. E.; Kardiman, C; Hutton, C. A. Tetrahedron Lett. 2004, 45, 6657).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 53087-13-1.

Reference:
Patent; The Procter & Gamble Company; US2007/209123; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 53087-13-1, A common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, molecular formula is C13H11BrO, 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.

Iodine, warmed up with magnesium, was added to a suspension of magnesium tunings (1 .29 g, 52.8 mmol) in dry THF (50 ml_). The mixture was refluxed and about 5% of a solution of 3- bromophenol (13.9 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 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 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 (Na2S04), filtered and concentrated. The product was purified by silica gel chromatography (isohexane / EtOAc), which gave the title compound (8.5 g, 54%).

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; MEDIVIR AB; BETHEL, Richard; ENEROTH, Anders; KLASSON, Bjoern; OeBERG, Fredrik; (73 pag.)WO2016/30335; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem