Category: ethers-buliding-blocks

1484-26-0, A common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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.

B. 3-Benzyloxyphenyl isocyante. To a stirred solution of 3-benzyloxyaniline (507 mg, 2.54 mmol) in toluene (5 mL) containing TEA (740 muL, 5.34 mmol) was added 20percent phosgene in toluene (1.5 mL, 2.83 mmol). The reaction was stirred for 20 h at rt. The organic layer was washed with H2O (20 mL), dried (MgSO4) and concentrated to give a clear brown oil (497 mg, 87percent). The material was used in subsequent steps without charaterization.

The synthetic route of 1484-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Butler, Christopher R.; Edwards, James P.; Fourie, Anne M.; Grice, Cheryl A.; Karlsson, Lars; Savall, Brad M.; Tays, Kevin L.; Wei, Jianmei; US2006/223792; (2006); A1;,
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458-52-6, A common compound: 458-52-6, name is 2-Fluoro-4-methoxyaniline, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Step A 2-Fluoro-4-methoxyphenylhydrazine With vigorous stirring, 9.15 g (0.065 mole) of 2-fluoro-4-methoxyaniline (Example 3, Step B) was added to 60 mL of concentrated hydrochloric acid that had been cooled to -10¡ã C. A solution of 4.83 g (0.070 mole) of sodium nitrite in 30 mL of water was slowly added dropwise, while the temperature was kept at or below -10¡ã C. Upon completion of addition, the reaction mixture was stirred at -10¡ã C. for one hour, after which 33.85 (0.150 mole) of tin(II) chloride dihydrate in 50 mL of concentrated hydrochloric acid Was added slowly, dropwise, while the temperature was kept below -5¡ã C. After the reaction mixture had stirred for one hour as it warmed to ambient temperature, the crude product was filtered from the mixture and dissolved in 250 mL of water. This solution was made basic with 4N sodium hydroxide and extracted with methylene chloride. The combined extracts were dried over anhydrous sodium sulfate and filtered. The filtrate was placed on a silica gel column and eluted with methylene chloride to remove colored impurities and then with ethyl acetate to obtain the desired product. The solvent was evaporated under reduced pressure to yield 6.30 g of 2-fluoro-4-methoxyphenylhydrazine. The NMR spectrum was consistent with the proposed structure.

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-Fluoro-4-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FMC Corporation; US5262390; (1993); A;,
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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. 21702-84-1 name is 2,4-Dibromo-1-methoxybenzene, 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. 21702-84-1

(ii) 4-Methoxgammaisophthalonitrile 2,4-Dibromo-l -methoxybenzene (25 g, 0.094 mol; see step (i) above) was dissolved in dry DMF (50 mL). CuCN (25.3 g, 0.283 mol) was then added and the resulting mixture was stirred at 120C for 15 h, before being cooled to RT. The crude mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel, using 25% ethyl acetate in petroleum ether as eluent, to yield the sub-title compound (7.1 g, 24%) as pale yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dibromo-1-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; WO2006/135316; (2006); 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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., 22236-10-8

A mixture of 4,6-dichloro-2-(cyclopropylethynyl)-5-fluoropyrimidine (241.0 mg, 1.04 mmol) and 4-difluoromethoxy aniline (707.0 mg, 4.45 mmol) in EtOH (2 mL) was stirred at reflux for 1 hour. After cooling, the mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over MgS04, then filtered and evaporated. The residual material was separated by silica gel column chromatography (eluting with 1 :20 and 1 : 10 ethyl acetate-hexane) to afford 6-chloro-2-(cyclopropylethynyl)- N-(4-(difluoromethoxy)phenyl)-5-fluoropyrimidin-4-amine (258.0 mg, 70%); MS m/z 354.2 (100) [M+H]+, 356.2 (40).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; PTC THERAPEUTICS, INC.; LEE, Chang-Sun; BAIAZITOV, Ramil; CAO, Liangxian; DAVIS, Thomas, W.; DU, Wu; LIU, Ronggang; MOON, Young-choon; PAGET, Steven, D.; REN, Hongyu; SYDORENKO, Nadiya; WILDE, Richard, Gerald; WO2014/81906; (2014); A2;,
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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. 366-99-4 name is 3-Fluoro-4-methoxyaniline, 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. 366-99-4

To a stirred suspension of isatoic anhydride (1.63 g, 10 mmol) in 15 mL dioxane at room temperature 111-03-PCT – P2338R1 – 02120.004WO1100 under nitrogen was added powdered sodium hydroxide (40 mg, 1 mmol) followed by 3-fluoro-4- methoxyaniline (1.41 g, 10 mmol). The mixture was immersed in a room temperature oil bath and slowly heated to reflux. Carbon dioxide gas evolution was evident. After stirring at reflux for 2 hours, the reaction was cooled to room temperature and inorganics were filtered off with dioxane. The filtrate was concentrated to dryness to a brown solid. The crude product was dissolved in a minimum of hot 95% EtOH and with cooling, crystals formed. The crystals were filtered off and rinsed with a minimum of ice cold 95% EtOH to give a tan solid (1.0 g, 39%). 1H -NMR (400 MHz, CDCl3) delta 7.66 (br s, IH), 7.50 (dd, IH), 7.44 (dd, IH), 7.26 (m, IH), 7.17 (m, IH), 6.95 (m, IH), 6.71 (m, 2H), 5.50 (br s, 2H), 3.89 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Fluoro-4-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; WO2007/146824; (2007); A2;,
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A common compound: 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 54314-84-0

PREPARATION 5 [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[4-(3-benzyloxypropoxy)benzoyl]-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate Scheme I, Step D: To a 0.5 L stirred round bottom, purged with nitrogen, charge in order: [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-(4-hydroxybenzoyl)-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate (13.58 mmol), acetonitrile (250 mL), and potassium carbonate (67.92 mmol). To this stirred solution, at room temperature, add 3-bromopropoxymethylbenzene (27.2 mmol) and heat at 60¡ã C. for 16 hours under nitrogen. Dilute with EtOAc (200 mL) and filter. Concentrate the filtrate and purify by flash chromatography (330 g silica gel) eluting with 2-40percent EtOAc/chloroform. Concentrate the product containing fractions to give the title compound (9.0 g. 90.79percent): mass spectrum (m/z): 730.4 (M+H).

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, 54314-84-0, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FIELDS, Todd; US2015/126469; (2015); A1;,
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321-28-8,Some common heterocyclic compound, 321-28-8, name is 1-Fluoro-2-methoxybenzene, molecular formula is C7H7FO, 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: Preparation of 3′-fluoro-4′-methoxy-acetophenone Aluminum chloride, (80.0 g, 0.6 mol) and chloroform (750 mL) were placed in a 2 L three-necked round bottom flask fitted with a mechanical stirrer and cooled by means of an ice bath. To the stirred solution acetyl chloride (51.0 g, 0.65 mol) was added dropwise, maintaining the temperature between 5-10 C. The mixture was stirred for 10 minutes at 5 C. before the dropwise addition at 5-10 C. of 2-fluoroanisole (62.6 g, 0.5 mol). The mixture was stirred at 0-10 C. for 1 hour and poured into ice (1 L). The resultant layers were separated and the aqueous layer was extracted with dichloromethane (2*250 mL). The combined organic layers were washed with water (2*150 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo to a volume of 300 mL. Hexanes were added and a white solid formed which was isolated by filtration and air dried. This material was recrystallized from a mixture of dichloromethane and hexanes to afford (77.2 g, 92%) of material suitable for use in the next step: mp 92-94 C.; 1 H NMR (DMSO-d6) 7.8 (m, 2H), 7.3 (t, 1H), 3.9 (s, 3H), 2.5 (s, 3H).

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

Reference:
Patent; G.D. Searle & Co.; US5760068; (1998); A;,
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6346-09-4, 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. 6346-09-4, name is 4,4-Diethoxybutan-1-amine, A new synthetic method of this compound is introduced below.

General procedure: To the cooled solution (5-8) of appropriate sulfonyl chloride (20 mmol) and triethylamine (3.5 ml) in dichloromethane (100 ml) 4,4-diethoxybutane-1-amine (3.4 g, 20 mmol) was added. Reaction mixture was stirred at room temperature for 12 h, washed with saturated NaHCO3 solution in water (100 ml). Organic layer was separated, dried over MgSO4 and evaporated to give target compounds 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:
Article; Gazizov, Almir S.; Smolobochkin, Andrey V.; Anikina, Ekaterina A.; Voronina, Julia K.; Burilov, Alexander R.; Pudovik, Michail A.; Synthetic Communications; vol. 47; 1; (2017); p. 44 – 52;,
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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. 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 103291-07-2

Example 41i 1-(3-Bromophenyl)-4-fluoro-1-(4-fluoro-3-methoxyphenyl)-1H-isoindol-3-amine tert-Butyllithium (3.68 mL, 5.89 mmol) was added dropwise to THF (10 mL) at -100 C. under an argon atmosphere. A solution of 4-bromo-1-fluoro-2-methoxybenzene (0.604 g, 2.95 mmol) in THF (5 ml) was added dropwise followed by the addition of (E)-N-((3-bromophenyl)(2-cyano-3-fluorophenyl)methylene)-2-methylpropane-2-sulfinamide (1 g, 2.46 mmol) in THF (5 ml). The resulting reaction mixture was left on the thawing cooling bath for 30 min then the cooling bath was removed and the mixture was stirred at r.t. for 1 h. Hydrogen chloride-methanol solution (11.78 mL, 14.73 mmol) was added and the resulting mixture was stirred at r.t. for 1 h. The mixture was concentrated and purified on a silica gel column eluding with 0-10% 0.1 M NH3 in MeOH in DCM to afford 0.98 g (93%) of the title compound. MS (ES+) m/z 429, 431 (M+H)+

The synthetic route of 103291-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; US2010/125082; (2010); A1;,
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2859-78-1, name is 4-Bromo-1,2-dimethoxybenzene, 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. 2859-78-1

General procedure: To a solution of 4-bromoanisole (200.8 mg, 1.09 mmol, 1.0 equiv) in acetonitrile (2 mL) was added N-chlorosuccinimide(NCS) (158.3 mg, 1.19 mmol, 1.1 equiv) at rt to give a slightly cloudy mixture. Chlorotrimethylsilane (TMSCl) (14 muL, 0.11 mmol, 0.1 equiv) was then added drop-wise to the reaction mixture. Within a few minutes, the reaction mixture became clear pale yellow solution. The mixture continued to stir at rt for 1 h and was diluted with hexane. The biphasic mixture was concentrated on a rotary evaporator to a crude white solid-oil mixture. This mixture was taken up in hexane and filtered through a short plug of SiO2 and eluted with 5-10% EtOAc-hexane solution. The clear filtrate was concentrated to obtain a mixture of 4-bromo-2-chloro-1-methoxybenzene (2a-Cl) and 2,4-dichloro-1-methoxybenzene (2a-diCl) 237.0 mg (88% of 2a-Cl and 11% of 2a-diCl,based on NMR ratio 2a-Cl: 2a-diCl = 7.1: 1.0; as a pale yellow solid).

Statistics shows that 2859-78-1 is playing an increasingly important role. we look forward to future research findings about 4-Bromo-1,2-dimethoxybenzene.

Reference:
Article; Maibunkaew, Tapanee; Thongsornkleeb, Charnsak; Tummatorn, Jumreang; Bunrit, Anon; Ruchirawat, Somsak; Synlett; vol. 25; 12; (2014); p. 1769 – 1775;,
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