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.

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. 4.6.1. 5-(Benzyloxy)-8-methylbicyclo[4.2.0]octa-1,3,5-trien-7-one (9). Compound 9 was obtained as light yellow oil (271 mg) from 6d and tert-butyl((1-methoxyprop-1-en-1-yl)oxy)dimethylsilane in 23% yield, Rf=0.6 (Hexane/EtOAc=5:1); 1H NMR (400 MHz, CDCl3) delta 7.48-7.30 (m, 6H), 7.02 (d, J7.0 Hz, 1H), 6.89 (d, J8.4 Hz, 1H), 5.45 (s, 2H), 4.21 (q, J7.2 Hz, 1H), 1.47 (d, J7.2 Hz, 3H). 13C NMR (101 MHz, CDCl3) delta 189.3 (s), 157.0 (s), 152.6 (s), 137.8 (s), 136.4 (s), 130.7 (s), 128.5 (s), 128.2 (s), 127.9 (s), 116.7 (s), 114.2 (s), 74.0 (s), 58.3 (s), 15.0 (s). IR: gamma 2964, 2927, 2360, 2342, 1756, 1602, 1571, 1473, 1452, 1386, 1273, 1161, 1125, 991, 886, 795, 767, 748, 699 cm-1. HRMS calcd for C16H14NaO2 [M+Na]+: 261.0886, found: 261.0879.

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

Reference:
Article; Chen; Savage, Nikolas A.; Dong, Guangbin; Tetrahedron; vol. 70; 27-28; (2014); p. 4135 – 4146;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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., name: 1-(Benzyloxy)-3-bromobenzene

A degassed mixture of 3-benzyloxy-phenyl bromide (28) (0.2 g, 0.76 mmol), 3- cyanophenylboronic acid (0.223 g, 1.52 mmol), barium hydroxide (0.285 g, 1.67 mmol), Pd(PPh3)4 (0.088 g, 0.076 mmol), DME (5 mL) and H2O (3 mL) was heated (800C) for 6 hours with vigorous stirring under an argon atmosphere. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through a plug of celite. The filtrate was diluted with brine; the organic phase was separated, dried (MgSO4) and concentrated in vacuo. The residue obtained was purified by flash column chromatography (20% diethyl? ether-hexane) to give 75 (0.130 g, 60% yield) as a viscous liquid. 1H NMR (500 MHz, CDCl3) delta 7.85 (t, J = 2.5 Hz, IH), 7.78 (dt, J = 7.5 Hz, J = 1.5 Hz, IH), 7.63 (dt, J = 8.0 Hz, J = 1.5 Hz, IH), 7.53 (t, J = 8.0 Hz, IH), 7.46 (d, J = 7.5 Hz, 2H)5 7.44- 7.37 (m, 3H)5 7.35 (t, J = 7.0 Hz, IH), 7.18-7.14 (m, 2H), 7.02 (dd, J = 8.5 Hz5 J = 2.5 Hz, IH)5 5.17 (s, 2H).

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

Reference:
Patent; UNIVERSITY OF CONNECTICUT; WO2008/13963; (2008); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference 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.

Step3. 4-(4-morpholinyl)-1-{3-[(phenylmethyl) oxy] phenyl}-1-butanone Under argon, to a solution of 1-bromo-3-[(phenylmethyl) oxy] benzene (2.04 g, 7.76 mmol) in THF (30 mL) at-78 C, was added dropwise n-BuLi (5.1 mL, 1.6 M in Hexanes), 20 min after the addition, this solution was added to a solution the product from Step 3 (1.68 g, 7.76 mmol) in THF (30 mL) under argon at-78 C. 15 min later, the reaction mixture was slowly warmed to 0 C. The reaction mixture was poured into a mixture of EtOAC and NH4C1, then extracted with EtOAC (2X), organic layers were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was then purified with flash chromatography (hexanes/ethyl acetate 1: 4), to afford the title compound as a colorless oil (932 mg, 35%).

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/37197; (2005); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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., Product Details of 53087-13-1

A 1 L round-bottomed flask was charged with 1-(benzyloxy)-3-bromobenzene (45.5 g, 173 mmol), tert-amyl alcohol (200 mL) and dioxane (400 mL), and the contents were sparged with N2 for 45 minutes. A 3 L round-bottomed flask was charged with potassium phosphate tribasic (92 g, 433 mmol), 1,3-cyclohexanedione (97 weight %, 20 g, 173 mmol), palladium(II) acetate (0.78 g, 3.5 mmol) and 2-(di-tert-butylphospino)-2?-methylbiphenyl (2.16 g, 6.9 mmol), and the contents were sparged with N2 for 45 minutes. The solution of 1-(benzyloxy)-3-bromobenzene was then transferred to the 1,3-cyclohexanedione mixture via cannula, and the reaction mixture was heated to reflux overnight. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate (600 mL) and 10% hydrochloric acid (600 mL) with mixing. The lower aqueous layer was separated and extracted with ethyl acetate (600 mL). The combined organic layers were washed with brine (2×100 mL) and concentrated under reduced pressure. The residue was taken up in toluene (300 mL) and again concentrated under reduced pressure. The residue was taken up in toluene (300 mL) and warmed to 50 C. After cooling to room temperature, the solids were collected by filtration, washed with toluene (2×50 mL) and dried in a vacuum oven at 50 C. to give the titled compound (44.6 g, 88%). 1H NMR (400 MHz, DMSO-d6) delta ppm 10.54 (bs, 1H), 7.46-7.28 (m, 5H), 7.19-7.13 (m, 1H), 6.84-6.79 (m, 1H), 6.75-6.72 (m, 1H), 6.71-6.66 (m, 1H), 5.03 (s, 2H), 2.76-2.13 (m, 4H), 1.99-1.86 (m, 2H); MS (CI-NH3) m/z 312.0 (M+NH4)+.

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; AbbVie Inc.; Reata Pharmaceuticals, Inc.; Donner, Pamela; Wagner, Rolf; Shanley, Jason; Heyman, Howard; Krueger, Allan; Chen, Hui-Ju; Rozema, Michael; Grampovnik, David; Visnick, Melean; Anderson, Eric; Jiang, Xin; Bender, Christopher F.; Bolton, Gary Louis; Caprathe, Bradley William; Lee, Chitase; Roark, William Howard; US2015/225397; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. Recommanded Product: 1-(Benzyloxy)-3-bromobenzene

The 2-(3-hydroxyphenyl)-2,3-dimethoxypropan-1-ol, used as a starting material, was obtained as follows: Methoxyaceonitrile (14 g) in tetrahydrofuran (10 ml) was added to a solution of 3-benzyloxyphenylmagnesium bromide [prepared by heating a mixture of 3-benzyloxybromobenzene (52.6 g), magnesium powder (4.8 g) and tetrahydrofuran (250 ml) to 60 C. for 3 hours] in tetrahydrofuran and the mixture was heated to 60 C. for 30 minutes. The mixture was cooled to ambient temperature and acidified by the addition of 3N hydrochloric acid solution (250 ml). The mixture was extracted with diethyl ether. The organic phase was washed with water and with a saturated aqueous sodium chloride solution, dried (MgSO4) and evaporated. The residue was purified by column chromatography using a 19:1 v/v mixture of methylene chloride and diethyl ether as eluent. There was thus obtained 3-benzyloxyphenyl methoxymethyl ketone (32.3 g, 63%), as an orange oil.

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

Reference:
Patent; Imperial Chemical Industries PLC; ICI Pharma; US5132328; (1992); A;,
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.

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;,
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.

General procedure: All glassware used in the following procedure was flame dried and then cooled under nitrogen prior to use. A portion (1 mmol) of the required aryl bromide (10.00 mmol) was added to a suspension of magnesium turnings (250 mg, 10.5 mmol) in tetrahydrofuran (12 mL) containing a few iodine crystals and the mixture gently heated whilst stirring vigorously. Once the reaction forming the Grignard reagent had initiated (reflux became self-sustaining) the remaining bromobenzene was added dropwise at such a rate that gentle reflux was maintained. The mixture was then heated at reflux until the magnesium was consumed (usually 30-60 min) and then was cooled for 30 min using an ice bath. A solution of 1-benzyl 4-piperidone (5.00 – 6.25 mmol) in tetrahydrofuran (8 mL) was added dropwise over 1-2 h and the mixture was stirred for 1 h and then the ice bath was removed and the reaction mixture allowed to warm to room temperature whilst stirring for at least a further 2 h. The reaction was quenched by the addition of saturated ammonium chloride solution (60 mL) and extracted into diethyl ether (2 × 30 mL) followed by ethyl acetate (3 × 30 mL). The organic phases were combined and subjected to standard work up conditions to give the required crude product. Purification of the title compound was achieved by flash chromatography on silica or, where indicated, by elution through a short length silica column using the eluant specified. In some cases, the crude piperidinol was dehydrated directly without purification as indicated.

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

Reference:
Article; Conway, Richard J.; Valant, Celine; Christopoulos, Arthur; Robertson, Alan D.; Capuano, Ben; Crosby, Ian T.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 7; (2012); p. 2560 – 2564;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. name: 1-(Benzyloxy)-3-bromobenzene

Preparation 3 3-Benzyloxyphenyl boronic acid A solution of 3-benzyloxy-bromobenzene 10 g (38 mmol) in 150 mL of anhydrous THF was cooled to -70C under a nitrogen atmosphere. 28.5 mL of n-butyl lithium (1.6 M in hexanes) was added dropwise to the solution. The reaction mixture was stirred for 30 minutes, then tri-isopropyl borate 10.6 mL (45.6 mmol) was added. The reaction mixture was allowed to warm to ambient temperature over a two hour period. The reaction was quenched by the addition of 200 mL of 1 N HCl andthe reaction mixture was stirred for an additional hour. The slurry was extracted twice with EtOAc and the organic layer separated and combined. The EtOAc solution was washed twice with brine, dried with Na2SO4, and evaporated to a yellow oil. The product was crystallized from ether-hexane. This yielded 4.85 g of the title compound as white solid. PMR: Consistent with the proposed structure.

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; ELI LILLY AND COMPANY; EP838461; (1998); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 53087-13-1 as follows. COA of Formula: C13H11BrO

Preparation 3 3-Benzyloxyphenyl Boronic Acid A solution of 3-benzyloxy-bromobenzene 10 g (38 mmol) in 150 mL of anhydrous THF was cooled to -70 C. under a nitrogen atmosphere. 28.5 mL of n-butyl lithium (1.6M in hexanes) was added dropwise to the solution. The reaction mixture was stirred for 30 minutes, then tri-isopropyl borate 10.6 mL (45.6 mmol) was added. The reaction mixture was allowed to warm to ambient temperature over a two hour period. The reaction was quenched by the addition of 200 mL of 1N HCl and the reaction mixture was stirred for an additional hour. The slurry was extracted twice with EtOAc and the organic layer separated and combined. The EtOAc solution was washed twice with brine, dried with Na2 SO4, and evaporated to a yellow oil. The product was crystallized from ether-hexane. This yielded 4.85 g of the title compound as white solid. PMR: Consistent with the proposed structure.

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.

Synthetic Route of 53087-13-1, 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. 53087-13-1 name is 1-(Benzyloxy)-3-bromobenzene, 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.

1-Benzyloxy-3-bromobenzene (10.56 g, 40.13 mmol), 3,5-dimethoxybenzaldehyde (7.34 g, 44.14 mmol), and n-butyl lithium (17.66 ml, 44.14 mmol) were treated in the same manner as described above for the synthesis of (2,3-dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanol. The crude material was purified via flash column chromatography (10% EtOAc in hexane gradient to 40% EtOAc in hexane in about 40 min.) to give (3-Benzyloxy-phenyl)-(3,5-dimethoxy-phenyl)-methanol as an oil (11.54 g, 82%): 1H-NMR (CDCl3) 7.43-7.21 (m, 6H, Ar), 7.04-6.85 (m, 3H, Ar), 6.54 (d, J=2 Hz, 2H, Ar), 6.36 (t, J=2 Hz, 1H, Ar), 5.72 (d, J=3 Hz, 1H, CHOH), 5.04 (s, 2H, CH2), 3.76 (s, 6H, 2OCH3), 2.21 (d, J=3 Hz, 1H, OH). The product was carried over to the next step.

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.