Category: 3401-47-6

Electric Literature of 3401-47-6, A common heterocyclic compound, 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, molecular formula is C11H9BrO, 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] Synthesis of 1-(2-Fluorophenyl)-2-methoxynaphthalene Into a 500 mL three-neck flask were placed 8.7 g (35 mmol) of 1-bromo-2-methoxynaphthalene, and 5.0 g (35 mmol) of 2-fluorophenylboronic acid. The air in the flask was replaced with nitrogen. To this mixture were added 120 mL of toluene, 60 mL of ethanol, and 40 mL of an aqueous solution of sodium carbonate (2.0 mol/L). While the pressure was reduced, this mixture was stirred to be degassed. To this mixture was added 2.0 g (1.7 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 80 C. for 8 hours under a nitrogen stream. The aqueous layer of the obtained mixture was subjected to extraction with toluene, and the obtained solution of the extract and the organic layer were combined and washed with saturated brine. The organic layer was dried with magnesium sulfate, and this mixture was gravity-filtered. An oily substance obtained by concentration of the obtained filtrate was dissolved in about 30 mL of toluene. This solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). An oily substance obtained by concentration of the obtained filtrate was dried under reduced pressure, so that 5.3 g of a pale yellow oily substance of the object of the synthesis was obtained in 60% yield. The reaction scheme of Step 1 is illustrated in (E2-1).

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; Semiconductor Energy Laboratory Co., Ltd.; US2012/165550; (2012); A1;,
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. 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Bromo-2-methoxynaphthalene

In a glove box, 1.0 mmol of 1-bromo-2-methoxynaphthalene, 2.0 mmol of aryl boronic acid, Pd2 (dba) 3, phosphine ligand and 3.0 mmol of potassium phosphate were charged in 7 mL of anhydrous toluene under nitrogen , And the temperature was raised to 80 C, and the reaction was carried out for a period of time. The results are shown in Table 2 below.The amount of Pd2 (dba) 3 and the phosphine ligand is divided into two kinds: (1) 0.25 mol% Pd2 (dba) 3, 0.5 mol% phosphine ligand, or (2) 0.5 mol% Pd2 (dba) mol% phosphine ligand, depending on the amount of ligand used in Table 2.

According to the analysis of related databases, 3401-47-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sun Yat-sen University; Qiu Liqin; Yu Sifan; Zhou Xiantai; (23 pag.)CN106995461; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 3401-47-6, 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. 3401-47-6 name is 1-Bromo-2-methoxynaphthalene, 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.

In a glove box, 1.0 mmol of 1-bromo-2-methoxynaphthalene, 2.0 mmol of aryl boronic acid, Pd2 (dba) 3, phosphine ligand and 3.0 mmol of potassium phosphate were charged in 7 mL of anhydrous toluene under nitrogen , And the temperature was raised to 80 C, and the reaction was carried out for a period of time. The results are shown in Table 2 below.The amount of Pd2 (dba) 3 and the phosphine ligand is divided into two kinds: (1) 0.25 mol% Pd2 (dba) 3, 0.5 mol% phosphine ligand, or (2) 0.5 mol% Pd2 (dba) mol% phosphine ligand, depending on the amount of ligand used in Table 2.

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

Reference:
Patent; Sun Yat-sen University; Qiu Liqin; Yu Sifan; Zhou Xiantai; (23 pag.)CN106995461; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 3401-47-6,Some common heterocyclic compound, 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, molecular formula is C11H9BrO, 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: The mixture of anisole(1c, 0.216 mg, 2 mmol) and acetyl chloride (2a, 0.157 mg, 2 mmol) was treated with CTAB/CTAC, (0.001 mol), in dichloroethane and the resulting reaction mixture was heated in a controlled microwave synthesizer (BiotageInitiator+SP Wave model (0.200W at 2.45 GHz, capped at 60W duringsteady state) for 5 min (attains temperature 100 C and 2 bar pressure). The final product (3o) was isolated by absorbing the reaction mixture into silica geland purifying it by column chromatography using ethyl acetate-petroleumether as the eluent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2-methoxynaphthalene, its application will become more common.

Reference:
Article; Rajendar Reddy; Rajanna; Uppalaiah; Tetrahedron Letters; vol. 54; 26; (2013); p. 3431 – 3436;,
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 3401-47-6 as follows. Product Details of 3401-47-6

A mixture of 1-bromo-2-methoxynaphthalene (1.0 equiv.), Phenylboronic acid (1.5 equiv.) And K3PO4(3 equiv.), Toluene (2 mL / mmol of aryl bromide) and a catalyst (Pd content of 0.001 mol%) were added to a dry reaction tube with a magnetic stir bar.The reaction tube was then stirred at 100 C for 24 h under an argon atmosphere.After the reaction, the solution was cooled to room temperature, 5 mL of water was added and the mixture was extracted with 3 x 5 mL of ethyl acetate. The organic phases were combined and the organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated by rotary evaporation. chromatography to give the desired product(yield 28%).

According to the analysis of related databases, 3401-47-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SOOCHOW UNIVERSITY; LANG, JIANPING; NING, JINJIAO; REN, ZHIGANG; (13 pag.)CN104710255; (2016); B;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 3401-47-6, A common heterocyclic compound, 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, molecular formula is C11H9BrO, 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] Synthesis of 1-(2-Fluorophenyl)-2-methoxynaphthalene Into a 500 mL three-neck flask were placed 8.7 g (35 mmol) of 1-bromo-2-methoxynaphthalene, and 5.0 g (35 mmol) of 2-fluorophenylboronic acid. The air in the flask was replaced with nitrogen. To this mixture were added 120 mL of toluene, 60 mL of ethanol, and 40 mL of an aqueous solution of sodium carbonate (2.0 mol/L). While the pressure was reduced, this mixture was stirred to be degassed. To this mixture was added 2.0 g (1.7 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 80 C. for 8 hours under a nitrogen stream. The aqueous layer of the obtained mixture was subjected to extraction with toluene, and the obtained solution of the extract and the organic layer were combined and washed with saturated brine. The organic layer was dried with magnesium sulfate, and this mixture was gravity-filtered. An oily substance obtained by concentration of the obtained filtrate was dissolved in about 30 mL of toluene. This solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). An oily substance obtained by concentration of the obtained filtrate was dried under reduced pressure, so that 5.3 g of a pale yellow oily substance of the object of the synthesis was obtained in 60% yield. The reaction scheme of Step 1 is illustrated in (E2-1).

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; Semiconductor Energy Laboratory Co., Ltd.; US2012/165550; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 3401-47-6, These common heterocyclic compound, 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, 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.

General procedure: The mixture of anisole(1c, 0.216 mg, 2 mmol) and acetyl chloride (2a, 0.157 mg, 2 mmol) was treated with CTAB/CTAC, (0.001 mol), in dichloroethane and the resulting reaction mixture was heated in a controlled microwave synthesizer (BiotageInitiator+SP Wave model (0.200W at 2.45 GHz, capped at 60W duringsteady state) for 5 min (attains temperature 100 C and 2 bar pressure). The final product (3o) was isolated by absorbing the reaction mixture into silica geland purifying it by column chromatography using ethyl acetate-petroleumether as the eluent.

Statistics shows that 1-Bromo-2-methoxynaphthalene is playing an increasingly important role. we look forward to future research findings about 3401-47-6.

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. 3401-47-6, name is 1-Bromo-2-methoxynaphthalene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 3401-47-6

General procedure: An oven-dried vial (35×12 mm) equipped with a PTFE-sealedxscrew cap was loaded with a magnetic stirrer bar, ((+/-)-binap)Ni[P(OPh)3]2*2PhCH3 (9) (39 mg, 25 mmol, 5mol-%), (+/-)-binap (15 mg, 25 mmol, 5 mol-%), and the corresponding aryl halide (0.50 mmol, 1.0 equiv.). The vial was then transferred into an argon-filled glovebox, where NaOtBu (216 mg, 2.20 mmol, 4.40 equiv.) and NH3 (0.5 M in 1,4-dioxane, 3.0 mL, 1.5 mmol, 3.0 equiv.) were added. The reaction vial was capped, removed from the glovebox, and placed into a preheated oil bath at 120 C to stir for 18 h. On cooling, the reaction mixture was diluted with Et2O (15 mL), and washed with 1 M NaOH (10 mL) and H2O (210 mL). The organic layer was fused onto silica and purified via flash column chromatography (EtOAc/hexanes or EtOAc/MeOH) to give the corresponding aniline. 2-Methoxynaphthalen-1-amine (19l) Following the general procedure using 1-bromo-2-methoxynaphthalene (119 mg, 0.500 mmol), the desired compound 19l was obtained after purification via flash column chromatography(hexanes/EtOAc 90 : 10) as a dark-orange oil (62 mg, 0.36 mmol, 72 %). The spectral data were in accordance with those reported in the literature.[65] Rf 0.22 (hexanes/EtOAc 90 : 10). deltaH (CDCl3, 500 MHz) 7.80-7.77 (2H, m, 2Ar-H), 7.46-7.42 (1H, m, Ar-H), 7.38-7.33 (2H, m, 2Ar-H), 7.26 (1H, d, J 8.8, Ar-H), 4.23 (2H, br s, NH2), 3.98 (3H, s, OMe). deltaC (CDCl3, 125 MHz) 142.6 (Ar-C), 129.6 (Ar-C), 129.5 (Ar-C), 128.5 (Ar-CH), 125.1 (Ar-CH), 124.0 (Ar-C), 123.7 (Ar-CH), 120.4 (Ar-CH), 118.5 (Ar-CH), 113.7 (Ar-CH), 56.8 (OMe).

The synthetic route of 3401-47-6 has been constantly updated, and we look forward to future research findings.

Some common heterocyclic compound, 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, molecular formula is C11H9BrO, 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. SDS of cas: 3401-47-6

Under argon, in a flame-dried vessel, a solution of 1-bromo-2-methoxynaphthalene (7.67 g, 32.36) in THF (50 ml) was added dropwise to the magnesium (0.905 g, 37.2 mmol) in THF (15 ml). The reaction mixture was stirred at room temperature for 2 h then at 50C for 1h. It was then cooled to -78C and trimethylborate (11.4 ml, 101.7 mmol) was slowly added. After 2 h at -78C, the mixture was allowed to warm to room temperature and stirred overnight. After addition of water (40 ml), THF was removed under reduced pressure. The mixture was extracted with dichloromethane; the combined organic phases were dried over MgSO4, filtered and concentrated. Recrystallization from dichloromethane gave the boronic acid as a white powder (80% yield). 1H NMR (400.14 MHz, CDCl3): d = 4.08 (s, 3H), 6.22 (s, 2 H), 7.28 (d, J = 9.1 Hz, 1H), 7.34-7.43 (m, 1H), 7.47-7.56 (m, 1H), 7.80 (d, J = 8.1 Hz, 1H), 7.98 (d, J = 8.9 Hz, 1H), 8.86 ppm (d, J = 9.1 Hz, 1H); 13C{1H} NMR (75.47 MHz, [D6]DMSO): d = 56.1, 113.7, 121.8, 122.7, 125.8, 127.4, 127.8, 128.5, 129.4, 135.6, 159.0

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3401-47-6, its application will become more common.

Reference:
Article; Castillo, Angelica Balanta; Perandones, Bernabe F.; Zangrando, Ennio; Gladiali, Serafino; Godard, Cyril; Claver, Carmen; Journal of Organometallic Chemistry; vol. 743; (2013); p. 31 – 36;,
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. 3401-47-6, name is 1-Bromo-2-methoxynaphthalene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 3401-47-6

In a nitrogen filled glove box, aryl halide (0.5 mmol), if solid, boronic acid (0.75 mmol), KOH (1.0 mmol) and 4dIPr*oMe (0.005 mmol, 0.5 mol% or 0.01 mmol, 1.0 mol%) were added to a 1 dram vial equipped with a magnetic stir bar. Aryl chloride (0.5mmol), if liquid, was added by syringe, followed by THF (1 mL). The vial was sealed andstirred outside of the glove box at 80C for 12 hours. At this point, the vial was opened to air and diethyl ether (10 mL) and H20 (10 mL) were added to the reaction mixture. The aqueous phase was extracted with diethyl ether (3 x 10 mL). The combined organic phases were dried over MgSO4 and filtered. The supernatant was then passed through a pad of silica gel,followed by removal of the solvent under reduced pressure to give the organic product.?H NMR data for the following compounds were consistent with those published in Bastug & Nolan, 2014, Organometallics 33:1253-1258. Following General Procedure A, a mixture of 1-bromo-2-methoxynaphthalene (118 mg, 0.5 mmol), 2,3,5,6-tetramethylphenyl boronic acid (133 mg, 0.75 mmol), potassium hydroxide (56 mg, 1.0 mmol), 4dIPr*oMe (3.2 mg, 0.0025 mmol) and THF (1 mL) was stirred at 80C for 12 hours. The average of two runs provided a yield of 94% (136 mg).

The synthetic route of 3401-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YALE UNIVERSITY; HAZARI, Nilay; MELVIN, Patrick; HRUSZKEWYCZ, Damian; (92 pag.)WO2016/57600; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem