Author: Jessica.F

Reference of 105404-89-5, A common heterocyclic compound, 105404-89-5, name is 2,7-Dibromo-3,6-dimethoxynaphthalene, molecular formula is C12H10Br2O2, 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.

Into a 200-mL three-neck flask were put 3.0 g (8.7 mmol) of3,6-dibromo-2,7-dimethoxynaphthalene, 1.2 g (8.7 mmol) of 2-fluorophenylboronic acid, 2.4 g(17 mmol) of potassium carbonate, and 0.13 g (0.43 mmol) of tris(2-methylphenyl)phosphine.5 To this mixture was added 90 mL of toluene. The resulting mixture was degassed by beingstirred while the pressure was reduced. To the mixture was added 19 mg (87 IJ.mol) ofpalladium(II) acetate, and stirring was performed under a nitrogen stream at 110 oc for 7 hours.After the stirring, toluene was added to the mixture, and the resulting mixture wassuction-filtered through Florisil (manufactured by Wako Pure Chemical Industries, Ltd., Catalog10 No. 540-00135), Celite (manufactured by Wako Pure Chemical Industries, Ltd., Catalog No.531-16855), and alumina to give a filtrate. The filtrate was concentrated to give a solid. Thissolid was purified by silica gel column chromatography (as the developing solvent, first, tolueneand hexane in a ratio of 1:2 were used, and then toluene and hexane in a ratio of 1:1 were used)to give 1.1 g of a white solid which was an objective substance in a yield of 34 %. A synthesis15 scheme of Step 1 is shown below

The synthetic route of 105404-89-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SEMICONDUCTOR ENERGY LABORATORY CO., LTD.; TAKEDA, Kyoko; OSAKA, Harue; SEO, Satoshi; SUZUKI, Tsunenori; HASHIMOTO, Naoaki; TAKITA, Yusuke; (225 pag.)WO2018/167612; (2018); A1;,
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Some common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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: 4-Bromo-2-methoxyaniline

a) tert-Butyl N-(4-bromo-2-methoxyphenyl)carbamate. A mixture of 4-bromo-2-methoxyaniline (34.0 g, 0.17 mol) and di-tert-butyl dicarbonate (44.5 g, 0.20 mol) in tetrahydrofuran (350 ml) was heated at reflux for 22 h. The mixture was allowed to cool to ambient temperature and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (350 ml) and washed with 1 N citric acid (200 ml), dried over magnesium sulfate, filtered and evaporated to give tert-butyl N-(4-bromo-2-methoxyphenyl)carbamate as a yellow oil (80% pure, 57.10 g, 0.15 mol): 1H NMR (DMSO-d6, 400 MHz) delta 8.01 (s, 1H), 7.63 (d, 1H), 7.17 (d, 1H), 7.07 (dd, 1H), 3.82 (s, 3H), 1.45 (s, 9H); TLC (n-heptane/ethyl acetate=2:1) Rf 0.67.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59557-91-4, its application will become more common.

Reference:
Patent; CALDERWOOD, DAVID; ARNOLD, LEE; MAZDIYASNI, HORMOZ; HIRST, GAVIN C.; DENG, BOJUAN B.; JOHNSTON, DAVID N.; RAFFERTY, PAUL; TOMETZKI, GERALD B.; TWIGGER, HELEN L.; MUNSCHAUER, RAINER; US2003/187001; (2003); A1;,
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Reference of 19500-02-8, 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. 19500-02-8, name is 3-Methoxy-2-methylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Part A Preparation of N-tert-butoxycarbonyl-3-methoxy-2-methylaniline. A solution of 44.4 g (344 mmol) of 3-methoxy-2-methylaniline and 75 g (344 mmol)of di-tert-butyl dicarbonate in 400 mL of THF was heated to maintain reflux for 4 hours. After concentrating at reduced pressure, the residue was taken up in ethyl acetate, washed with iN citric acid, water and dried (MgSO4). After removing the solvent at reduced pressure, the residue was crystallized from hexane to give 64.5 g (84percent yield) of N-tert-butoxycarbonyl-3-methoxy-2-methylaniline, mp, 56-57¡ã C. Analysis for C13H19NO3: Calculated: C, 65.80; H, 8.07; N, 5.90 Found: C, 63.32; H, 7.83; N, 5.56.

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

Reference:
Patent; Eli Lilly and Company; US6274578; (2001); B1;,
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Related Products of 171290-52-1,Some common heterocyclic compound, 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, molecular formula is C10H10O2, 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.

3,5-dimethoxyphenylacetylene 81 mg (0.50 mmol), silver nitrite 154 mg (1 mmol), N-bromosuccinimide 178 mg (1 mmol)10 mL of a pressure-tight sealed container was sequentially added, and 5 mL of 1,2-dichloroethane was further added.The mixture was stirred at room temperature, and the reaction was checked by TLC. The reaction was completed in 8 hours.The reaction solution was diluted with 10 mL of dichloromethane, and filtered to give a clear liquid.Separation by column chromatography (extraction of petroleum ether/ethyl acetate in a volume ratio of 100:1)The eluate containing the desired product were collected and the solvent was evaporated to give a white solid 3,5-dimethoxy-benzonitrile 42.4mg (52% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dimethoxyphenylacetylene, its application will become more common.

Reference:
Patent; Zhejiang University of Technology; Liu Yunkui; Zhang Jian; Bao Hanyang; (9 pag.)CN107641088; (2018); A;,
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Reference of 5467-58-3, These common heterocyclic compound, 5467-58-3, name is 1-Bromo-4-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.

Under a nitrogen atmosphere,Add 1-bromo-4-methoxynaphthalene (42.4 mg, 0.18 mmol) to a 25 mL sealed tube.Dichloroethane 2.0 mL, N-trifluoromethoxy-2,6-dichloropyridine hexafluoroantimonate (101 mg, 0.22 mmol) was added at 80 C for 36 hours. After adding 1.0 mL of a saturated aqueous solution of sodium hydrogencarbonate and 8.0 mL of distilled water, it was extracted with dichloromethane (15 mL ¡Á 3), washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. Filter and spin dry the solvent. Column chromatography gave 18.0 mg of 1-bromo-2-trifluoromethoxy-4-methoxynaphthalene in a yield of 31%. 10.8 mg of 1-bromo-3-trifluoromethoxy-4-Methoxynaphthalene, yield 19%. The total yield is 50%.

The synthetic route of 5467-58-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Mei Benzhaoxiong; Zhou Min; Hu Jinbo; (18 pag.)CN105017143; (2018); B;,
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1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C9H11BrO

Step 2 To an acetonitrile (250 mL) solution of crude product 2 (24.5 g) obtained from Step 1, benzyl-2-bromoethylether A (27.3 mL, 173 mmol) and potassium carbonate (27.5 g, 199 mmol) were added, under nitrogen atmosphere, followed by heating at reflux for 4 hours and a half. The reaction solution was filtered and then the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate, washed sequentially with water and saturated brine, then dried with anhydrous magnesium sulfate and concentrated in vacuo to yield crude product 3 (54.6 g). LC/MS (Method A): 1.97 min, [M+H]+ = 319.

The synthetic route of 1462-37-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi&Co., Ltd.; EP2327704; (2011); A1;,
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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. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Bromo-3,5-dimethoxybenzene

Condensation reaction: in with a thermometer, condenser 250 ml bottle to join four 21.9g 5 – bromo – m dimethyl ether {melting point 62 – 66 C; appearance: white solid; nuclear magnetic:1H NMR (CDCl3, 400MHz) delta (ppm) data are as follows: 3.82 (s, 6H, CH3), 6.37 (t, 1H, Ar – H), 6.81 (d, 2H, Ar – H)}, 12.8g bromopropylene, 20.4g triethylamine, 2.2g dppp nickel chloride, 130 ml methyl tert-butyl ether, magnetic stirring, oil bath heating, when the temperature rises to 50 C and maintaining at 4 hours, after the reaction is cooled to ambient temperature, for 60 ml 10% hydrochloric acid aqueous solution washing the reaction liquid, water washed to neutral, the organic layer is distilled under reduced pressure to obtain 17.4g 5 – propenyl – m dimethyl ether {melting point 97 – 100 C; appearance: white solid; nuclear magnetic resonance:1

According to the analysis of related databases, 20469-65-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Weifang Xian Da Chemical Co., Ltd.; Li Kai; Wang Guangyue; Yang Qiwei; Zou Yabo; (7 pag.)CN106748673; (2017); A;,
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These common heterocyclic compound, 538-86-3, name is (Methoxymethyl)benzene, 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. Quality Control of (Methoxymethyl)benzene

General procedure: The reactions were carried out a ~40 mL, Teflon-lined, stainlesssteelautoclave. AcOH (2 mL), TEMPO (0.25 mmol), HNO3 (0.25mmol), the appropriate benzylic methyl ether (0.5 mmol), andNH4OAc (1.5 mmol) were added sequentially to the autoclave.Subsequently, the autoclave was pressurized to 1 MPa with O2,and the reaction mixture was heated with magnetic stirring at50 ¡ãC for 20 h, then cooled to r.t. The mixture was then dilutedwith Et2O (15 mL) and H2O (5 mL), and adjusted to pH 7?8 with2 M aq NaOH. The two layers were separated, and the aqueouslayer was extracted with Et2O (3 ¡Á 15 mL). The organic layerswere combined, dried (Na2SO4), filtered, and concentrated to avolume of approximately 3 mL in a rotary evaporator. GC analysisof the concentrated organic phase, with biphenyl or 1,2,4,5-tetramethylbenzene as internal standard, provided the GC yieldof the product. The crude product in the concentrated organicphase from another parallel experiment was purified bycolumn chromatography [silica gel (200?300 mesh), EtOAc?PE].

The synthetic route of (Methoxymethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tian, Xinzhe; Ren, Yun-Lai; Ren, Fangping; Cheng, Xinqiang; Zhao, Shuang; Wang, Jianji; Synlett; vol. 29; 18; (2018); p. 2444 – 2448;,
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Synthetic Route of 1663-61-2,Some common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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 orthoester (1.5 equiv) was added to a mixture of the 2-aminobenzamide (1.0 equiv) in absoluteethanol (3 mL). Glacial acetic acid (2 equiv) was added and the reaction was heated at reflux for 12?24 h.The reaction mixture was cooled and concentrated under vacuum. If the crude product was pure by1H-NMR, it was triturated with 5percent ether in pentane. If it was not pure, it was recrystallized fromethanol. In some cases, it was necessary to remove excess orthoester under high vacuum at 50 ¡ãC prior to purification. The following compounds were prepared:

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gavin, Joshua T.; Annor-Gyamfi, Joel K.; Bunce, Richard A.; Molecules; vol. 23; 11; (2018);,
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