Category: ethers-buliding-blocks

39538-68-6, name is 2-Methoxy-4-methylaniline, 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. HPLC of Formula: C8H11NO

General procedure: To a magnetically stirred solution of the selected aromatic amine (0.01 mol) in anhydrous dioxane (30 ml), succinic anhydride (0.01 mol) was added and the resulting suspension was refluxed for 24 h. Subsequently, the reaction mixture was cooled to room temperature. Subsequently, petroleum ether (200 mL) was added to the reaction mixture to yield the succinic monoamide derivatives (112-119, see Scheme 2) as white to grey solids. Using the same general procedure, the following compounds were synthesized.

The synthetic route of 39538-68-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Habash, Maha; Taha, Mutasem O.; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 4746 – 4771;,
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Synthetic Route of 2741-16-4, 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. 2741-16-4, name is Isopropoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To 3-chloroperbenzoic acid dried in vacuo for 1 h prior to use (504mumol) in dry dichloromethane (5mL), was added 3-iododobenzoate succinimidyl ester (458mumol) and the solution was stirred at room temperature for 15min. Anisole (504mumol) was then added, the reaction cooled to -20C and triflic acid (916mumol) added. The solution turned dark. It was stirred for 15min at -20C and the volatiles were removed by rotary evaporation. To the dark residue was added Et2O. The thick oily suspension was stirred for about 45min upon which a deep blue precipitate formed. It was then purified by flash chromatography using aCH2Cl2/ tBuOH gradient from 95:5 to 60:40. The solid obtained was then recrystallized from CH3CN/Et2O to afford white crystals; 4.1.3 3-(Succinimidyloxycarbonyl)phenyl(4-isopropoxyphenyl)iodonium triflate (4b) The procedure was identical to the preparation of 4a, with anisole replaced by isopropoxybenzene and afforded 4b as colorless needles in 8% yield. 1H NMR (CD3CN, 400 MHz, ppm): delta 1.31 (d, 6H), 2.86 (s, 4H), 4.64-4.72 (m, 1H), 7.03 (d, 2H, J = 8.0 Hz), 7.72 (t, 1H, J = 8.0 Hz), 8.03 (d, 2H, J = 8.0 Hz), 8.35 (m, 2H), 8.74 (m, 1H). 13C NMR (CD3CN, 100 MHz, ppm): delta 21.9, 26.5, 72.0, 101.7, 115.1, 120.5, 123.6, 129.4, 134.0, 134.9, 137.0, 139.2, 141.7, 161.2, 163.1, 170.8. 19F NMR (CD3CN, 400 MHz, ppm): delta -79.70. HRMS: C20H19INO5+[M-OTf]+ calc: 480.0308, found: 480.0315

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, Isopropoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Guerard; Navarro; Lee; Roumesy; Alliot; Cherel; Brechbiel; Gestin; Bioorganic and Medicinal Chemistry; vol. 25; 21; (2017); p. 5975 – 5980;,
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Synthetic Route of 2944-49-2, 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. 2944-49-2 name is 1-Methoxy-2,3-dimethylbenzene, 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.

To a solution of the above crude product (2) (3.5g) in tetrachloromethane (C4Cl4) (100mL) at room temperature were added N-bromosuccinimide (NBS) (34.0g, 190.4mmol) and 2,2′-azobis(2-methylpropionitrile) (AIBN) (0.3g). The resulting reaction mixture was allowed to stir under reflux for 24h. After reaction completion, the reaction mixture was filtered and washed using the saturated NaHSO4 solution to remove the residual bromine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography to give a white solid (7.70 g, 72.4% in the two-step yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methoxy-2,3-dimethylbenzene, and friends who are interested can also refer to it.

Reference:
Article; Jin, Chaobin; Alenazy, Rawaf; Wang, Yinhu; Mowla, Rumana; Qin, Yinhui; Tan, Jin Quan Eugene; Modi, Natansh Deepak; Gu, Xinjie; Polyak, Steven W.; Venter, Henrietta; Ma, Shutao; Bioorganic and Medicinal Chemistry Letters; vol. 29; 7; (2019); p. 882 – 889;,
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Synthetic Route of 175278-09-8, 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. 175278-09-8, name is 4-Bromo-2-(trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows.

1b. Preparation of 1 -bromo-3-trifluoromethoxybenzene. 2579.53 g of 2-propanol and 1100 g of the product from stage Ia are placed in a 10 litre lined glass reactor with 4 necks and outlet on bottom, and a previously prepared solution of 382.52 g of NaNO2 in 766.18 g of water is added. 459.6 g of concentrated sulphuric acid are then metered slowly. The acids are diluted and the upper organic phase is separated from the lower aqueous phase. The organic phase is washed and a first organic phase and an upper aqueous phase are separated. The latter is further diluted with water until a second organic phase is released. This organic phase is added to the first and everything is washed again, separating an aqueous phase and an organic phase which, after being anhydrified with CaCl2, undergoes distillation to provide the product indicated in the title (final yield 84%). B.p. 156-158C/760 mmHg.

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2-(trifluoromethoxy)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MITENI S.P.A.; WO2007/107820; (2007); A2;,
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Application of 41365-75-7, 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 41365-75-7 as follows.

General procedure: A mixture of 0.6 mmol of quinomethane 1a-1c and 0.6 mmol of 3,3-diethoxypropan-1-amine (2) or 4,4-diethoxybutan-1-amine (3) in 1 mL of 1,4-dioxane was stirred for 2-3 h at room temperature under argon. When the reaction was complete, the solvent was removed under reduced pressure (water-jet pump), and the residue was washed with hexane and dried in a vacuum (oil pump) until constant weight.

According to the analysis of related databases, 41365-75-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Vagapova; Amirova; Burilov; Pudovik; Sinyashin; Russian Journal of Organic Chemistry; vol. 51; 9; (2015); p. 1268 – 1271; Zh. Org. Khim.; vol. 51; 9; (2015); p. 1294 – 1297,4;,
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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. 41365-75-7, name is 1-Amino-3,3-diethoxypropane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 41365-75-7

Intermediate 210: 6-Benzyl-/yt-(3,3-diethoxypropyn-/^-methylpyridine-2,4- dicarboxamide (1150) To a mixture of 2-benzyl-6-(methylcarbamoyl)isonicotinic acid (77.8 mg, 0.29 mmol) and HATU (142.9 mg, 0.38 mmol) in DMF (1.5 mL) was added 3,3-diethoxypropan-l-amine (0.061 mL, 0.37 mmol) and DIPEA (0.151 mL, 0.86 mmol). The mixture was stirred at rt for 4.5 h, after which the volatiles were evaporated under a stream of nitrogen. This was redissolved in DMSO (3 mL) and directly purified by MDAP (high pH). The required fractions were combined and evaporated in vacuo to give 6-benzyl-/V,-(3,3-diethoxypropyl)-Ae-methylpyridine-2,4-dicarboxamide (91.3 mg, 0.23 mmol, 79 % yield) a light brown gum. (1151) LCMS (2 min High pH): Rt = 1.08 min, [MH]+ = 400.4.

The synthetic route of 41365-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LEVERNIER, Etienne; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (225 pag.)WO2017/174621; (2017); A1;,
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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. 366-99-4, name is 3-Fluoro-4-methoxyaniline, A new synthetic method of this compound is introduced below., Quality Control of 3-Fluoro-4-methoxyaniline

Acetone (11.6 g, 200 mmol), Acetic acid (1.8 g, 30 mmol), and Sodium triacetoxyborohydride (6.36 g, 30 mmol) were added to a solution of 3-Fluoro-4-methoxyaniline (2.82 g, 20 mmol) in DCM (120 mL) and the mixture was stirred at RT for 12 hr. Water was added to quench the reaction and the mixture was extracted with DCM. The solvent was removed under and the residue was purified by silica gel chromatography to afford 3-Fluoro-N-isopropyl-4-methoxyaniline (2.90 g, 79percent yield). 1H NMR (400 MHz, CDC13) delta ppm 6.84 (dd, J= 9.5, 8.7 Hz, 1H), 6.41 (dd, J= 13.5, 2.7 Hz, 1H), 6.33- 6.27(m, 1H), 3.83 (s, 3H), 3.54-3.52(m, 1H), 3.28 (s, 1H), 1.21 (d, J= 6.3 Hz, 6H).

The synthetic route of 366-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JIANGSU ASCENTAGE BIOMED DEVELOPMENT INC.; CHEN, Jianyong; ZHOU, Yunlong; WANG, Shaomeng; GUO, Ming; YANG, Dajun; JIAO, Lingling; JING, Yu; QIAN, Xu; LIU, Liu; BAI, Longchuan; YANG, Chao-Yie; MCEACHERN, Donna; WO2015/127629; (2015); A1;,
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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;,
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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;,
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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. 22171-15-9, name is (4-(Benzyloxy)phenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 22171-15-9

2-Amino-6-chloro-nicotinic acid described in Preparation Example A-1 (220mg, 1.4mmol), triethylamine (0.47mL, 3.37mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (764mg, 1.73mmol) were dissolved in N,N-dimethylformamide (3mL), 4-benzyloxy-benzylamine described in Preparation Example 1 (399mg, 1.87mmol) was added thereto, followed by stirring at room temperature for 17 hours 30 minutes. After the reaction was completed, the reaction solution was poured into brine, which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then concentrated, the obtained residue was purified by silica gel column chromatography (ethyl acetate : hexane = 1 : 1), and the title compound (115mg, 0.31 mmol, 22%) was obtained. 1H-NMR Spectrum (DMSO-d6) delta(ppm): 4.35 (2H, d, J=6.0Hz), 5.08 (2H, s), 6.63 (1H, d, J=8.0Hz), 6.94-6.98 (2H, m), 7.23 (2H, d, J=8.4Hz), 7.29-7.45 (5H, m), 7.52 (2H, brs), 7.97 (1 H, d, J=8.0Hz), 8.96 (1 H, t, J=6.0Hz).

According to the analysis of related databases, 22171-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
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