Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 62257-15-2, name is 2-Fluoro-5-methoxyaniline, 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 62257-15-2, Safety of 2-Fluoro-5-methoxyaniline

B. Ethyl 5-amino-1-(2-fluoro-5-methoxyphenyl)-1H-imidazole-4-carboxylate, 3b A solution of compound 3a (4.5 g, 35 mmol) and (diethoxymethoxy)ethane (6.3 g, 42 mmol) in CH3CN (50 mL) was stirred at 80 qC for 1 h. The reaction mixture was allowed to cool to RT and treated with 2-fluoro-5-methoxyaniline (3.0 g, 21 mmol). The resulting solution was stirred overnight at RT and concentrated. The residue obtained was purified by flash chromatography (0-25% EtOAc/petroleum ether) on silica gel to obtain compound 3b as a light yellow solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C13H14FN3O3: 280.1 (M+H); found: 280.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Fluoro-5-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; HUANG, Hui; MEEGALLA, Sanath; PLAYER, Mark R.; (196 pag.)WO2017/27310; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 36865-41-5, A common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, molecular formula is C4H9BrO, 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.

A mixture of 5-bromo-2-chloro-phenol (10.00 g, 48.20 mmol, 1.00 eq), 1-bromo-3- methoxy-propane (14.75 g, 96.41 mmol, 2.00 eq) and K2C03 (19.99 g, 144.61 mmol, 3.00 eq) in acetone (100.00 mL) was stirred at 50 C for 15 h. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography eluted with PE to PE :EA=5: 1. 4-bromo- 1 -chloro-2-(3 -methoxypropoxy)benzene (13.40 g, 47.93 mmol, 99.44% yield) was obtained as a colorless oil which was confirmed by LC-MS and used directly in the next step. LC-MS: EW5403-239-P1ZO (M+H=278.9, M+2+H=280.9)

The synthetic route of 36865-41-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (81 pag.)WO2018/22282; (2018); A1;,
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Ether | (C2H5)2O – PubChem

Application of 36865-41-5,Some common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, molecular formula is C4H9BrO, 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 stirred solution of ethyl isonipecotate (22.0 grams, 140 mmol) in acetonitrile (250 mL) at room temperature was added cesium carbonate (97 grams, 298 mmol) followed by l-brom -3-methoxypropane (20 mL, 154 mmol) and the reaction mixture was heated to reflux for 4 hours. The reaction mixture was cooled to room temperature and filtered through a small pad of celite. The volatiles were removed under reduced pressure to obtain ethyl l-(3-methoxy propyl) piperidin-4-carboxylate (31.0 grams).Yield: 99 %.? – NMR (CDCI3): delta 4.12 (q, 2H), 3.41 (t, J = 6.4 Hz, 2H), 2.90 – 2.85 (m, 2H), 2.38 (t, J = 7.4 Hz, 2H), 2.34 – 2.20 (m, 1H), 2.05 – 1.93 (m, 2H), 1.92 – 1.85 (m, 2H), 1.80 – 1.70 (m, 4H), 1.23 (t, J = 7.1 Hz, 3H); Mass (m/z): 230 (M+H)+.

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-3-methoxypropane, its application will become more common.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; MOHAMMED, Abdul Rasheed; YARLGADDA, Suresh; RAVELLA, Srinivasa Rao; SHINDE, Anil Karbhari; KAMBHAMPATI, Ramasastri; ROAYALLEY, Praveen Kumar; JAYARAJAN, Pradeep; BHYRAPUNENI, Gopinadh; PATNALA, Sriramachandra Murthy; RAVULA, Jyothsna; JASTI, Venkateswarlu; WO2013/42135; (2013); A1;,
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Ether | (C2H5)2O – PubChem

Application of 59557-91-4, A common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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 A:To a round bottom flask at room temperature, containing formic acid (85%, 27 rrsL, 624.4 mmoi) was added acetic anhydride (16 mL, 169.5 mmoi) dropwise. The reaction stirred for 45 min. followed by the dropwise addition of a solution of 4-bromo- 2-methoxyaniline (9.01 g, 44.6 mmoi) in THF (56 mL). The reaction mixture was quenched with ice-water after 23 h and the resulting precipitate was filtered to afford compound 100.1 (9.20 g, 90%) as a brown solid.

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; SCHERING CORPORATION; WO2009/76352; (2009); A1;,
Ether – Wikipedia,
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Synthetic Route of 36942-56-0,Some common heterocyclic compound, 36942-56-0, name is 2-Bromo-4-methoxy-1-methylbenzene, molecular formula is C8H9BrO, 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 solution of compound 11 (100 mg, 0.21 mmol) and 3-methoxybenzeneboronic acid (49 mg, 0.32 mmol) in dioxane (5 mL) and H2O (0.5 mL) was added Na2CO3 (44 mg, 0.42 mmol) and LiCl (18 mg, 0.42 mmol). Under Ar, Pd(PPh3)4 (24 mg, 0.021 mmol) was added. The mixture was stirred for 12 h at 85C. Water was added. The resulting solution was extracted with ethyl acetate and washed with water and brine. The organic solution was dried over sodium sulfate, concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum/ethyl acetate 5:1) to give 67 mg of 12 (yield: 75%) as a colorless liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-methoxy-1-methylbenzene, its application will become more common.

Reference:
Article; Huang, Jing; Guo, Bin; Chu, Wen-Jing; Xie, Xin; Yang, Yu-She; Zhou, Xian-Li; Chinese Chemical Letters; vol. 27; 1; (2016); p. 159 – 162;,
Ether – Wikipedia,
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Synthetic Route of 645-36-3, 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. 645-36-3, name is 2,2-Diethoxyethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A three-neck flask was charged with Pd(OAc)2 (0.0182 mmol, 4.1 mg), BINAP (0.02 mmol, 12 mg) and NaO-t-Bu (1.274 mmol, 122 mg). The reaction mixture was stirred in toluene (20 mL) for 10 min at 80 C. A mixture of NH2CH2CH(OCH2CH3)2 (1.092 mmol, 159 muL) and the compound prepared as in Example 1 (0.91 mmol, 500 mg) in toluene (2 mL) was then slowly added dropwise via syringe to the reaction mixture. After addition, the mixture was heated at 80 C. with stirring for 2 h. The reaction mixture was cooled to room temperature. Et2O and water were added and the solution was partitioned between Et2O and water. The Et2O layer was washed with brine, dried over anhydrous Na2SO4 and concentrate to yield the title compound as a crude solid. The crude product was purified by column chromatography using 4:1 hexanes/EtOAc to yield the title compound as a colorless oil. [0215] 1H NMR (300 MHz, CDCl3) delta 7.12 (d, J=8.8 Hz, 1H), 6.53 (d, J=8.8 Hz, 1H) 6.38 (s, 1H), 4.68 (t, J=6.0 Hz, 1H), 3.80 (br, s, 1H), 3.75 (m, 2H), 3.60 (m, 2H), 3.22 (d, J=6.0 Hz, 2H), 2.91 (m, 2H), 2.50 (dd, J=18.0, 8.8 Hz, 1H), 2.42 (m, 1H), 2.35 (m, 1H), 2.20 (m, 1H), 2.151.94 (m, 3H), 1.721.38 (m, 6H), 1.25 (t, J=7.6 Hz, 6H), 0.98 (s, 3H) MS (m/z) M+Na (408), MH- (384).

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, 2,2-Diethoxyethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sui, Zhihua; Zhang, Xuqing; US2005/4090; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 54314-84-0, 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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 210.2 (9.9 g, 34.82 mmol, 1.00 equiv), N,N-dimethylformamide (200 mL). This was followed by the addition of NaH (1.25 g, 52.08 mmol, 1.50 equiv) at 0° C. in a water/ice bath. The mixture was stirred for 1 h at 0° C. To this was added [(3-bromopropoxy) methyl] benzene (11.92 g, 52.03 mmol, 1.50 equiv). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 200 mL of NH4Cl (aq). The resulting solution was extracted with 2×300 mL of ethyl acetate and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:15). This resulted in 3.3 g (22percent) of 210.3 as yellow oil.

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-Bromopropoxy)methyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gilead Apollo, LLC; Ghosh, Shomir; Greenwood, Jeremy Robert; Harriman, Geraldine C.; Leit De Moradei, Silvana Marcel; (290 pag.)US2017/166584; (2017); A1;,
Ether – Wikipedia,
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Some common heterocyclic compound, 156573-09-0, name is 1-Bromo-4-ethoxy-2,3-difluorobenzene, molecular formula is C8H7BrF2O, 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: C8H7BrF2O

First Step THF (100 ml) was added to 1-bromo-4-ethoxy-2,3-difluorobenzene (5.1 g) in a reaction vessel under an atmosphere of nitrogen, and the mixture was cooled to -78 C. n-Butyllithium (1.57 M, in a hexane solution) (13.8 ml) was added dropwise at a temperature of -70 C. or lower. The stirring was continued at -78 C. for another 2 hours, and 4-(3-propylcyclopentyl)-cyclohexanone (3.0 g) in a THF (10 ml) solution was added dropwise at a temperature of -70 C. or lower. After the mixture had been stirred at -78 C. for another 1 hour, it was warmed to room temperature, and a saturated aqueous solution of ammonium chloride (50 ml) was added. The mixture was separated, and the water layer was extracted with ethyl acetate three times, and then the combined organic layer was washed with brine. The solution was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane= 1/9 by volume) to give 1-(4-ethoxy-2,3-difluorophenyl)-4-(3-propylcyclopentyl)cyclohexanol (5.0 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 156573-09-0, its application will become more common.

Reference:
Patent; CHISSO PETROCHEMICAL CORPORATION; JNC CORPORATION; US2011/309300; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 39021-83-5, name is 1,4-Dimethoxy-2,3-dimethylbenzene, molecular formula is C10H14O2, 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. Recommanded Product: 1,4-Dimethoxy-2,3-dimethylbenzene

The compound 72 (5 g, 30.1 mmol) was dissolved in TFA (50 mL) and hexamine (4.7 g, 33.1 mmol) was added to the resulting solution. The reaction mixture was refluxed under dry conditions for 2 hours. The TFA was evaporated under reduced pressure and the residue was dissolved in EtOAc (100 mL) . and the The resulting organic solution was washed with water (3×50 mL) and then dried over Na2SO4. The solvent organic phase was evaporated concentrated in vacuum and the residue was subjected to silica gel column chromatography (petroleum ether/EtOAc 20: 1 to 10: 1) to giveproduct 73 (3.1 g, 53) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39021-83-5, its application will become more common.

Reference:
Patent; XW LABORATORIES, INC.; XW LABORATORIES INC.; XIANG, Jia-Ning; QI, Zude; NING, Dezheng; LIU, Xianbo; (152 pag.)WO2019/33330; (2019); A1;,
Ether – Wikipedia,
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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