Month: July 2021

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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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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Application of 1535-75-7, The chemical industry reduces the impact on the environment during synthesis 1535-75-7, name is 2-(Trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

General procedure: Acetamides (1a-1x, 1ab, 1ac and 1ba-1bc). To a solution of 2-phenylacetic acid (7.0mmol), 2-(trifluoromethoxy)aniline (7.7mmol) in anhydrous CH2Cl2 (25mL) were added EDCI (1.745g, 9.1mmol) and DMAP (256.6mg, 2.1mmol). The reaction mixture was stirred at room temperature overnight, diluted with HCl (1M) aqueous solution, and extracted with CH2Cl2 (3×25mL). The combined organic phase was washed with saturated NaHCO3 aqueous solution and brine, dried over anhydrous Na2SO4, and concentrated under vacuum. Purification by flash chromatography (Silica gel, petroleum ether: ethyl acetate=50: 1 as eluent) gave the corresponding 2-phenyl-N-[2-(trifluoromethoxy)phenyl]acetamide compound.

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-(Trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhao, Xiao-Jing; Zhao, Jie; Sun, Xin; Liu, Ji-Kai; Wu, Bin; Tetrahedron; vol. 73; 25; (2017); p. 3463 – 3477;,
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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. 101-84-8, name is Diphenyl oxide, A new synthetic method of this compound is introduced below., name: Diphenyl oxide

EXAMPLE 1; Catalyzed Bromination [0047] A reactor was configured from a 1 -liter Morton flask with a mechanical stirrer, thermometer, 60 mL addition funnel, and fractionation column (10″ x 1″ (ca. 25.4 cm x 2.54 cm) with 5 mm x 5 mm Raschig rings) topped by a O0C reflux condenser. The outlet of the condenser was connected to a H2O trap. A small N2 purge was added to the line from the condenser to the H2O trap. The reactor was charged with 3.5 g OfAlCl3 and 1577g of bromine (containing 11 ppm H2O). The addition funnel was charged with 47.04 g of diphenyl oxide.The reactor was heated to 550C and the diphenyl oxide was added drop-wise supersurface. The time for the initiation of the diphenyl oxide addition was noted. The reactor was heated by a mantle. Twenty-seven minutes into the diphenyl oxide feed, half of the diphenyl oxide had been added and the reaction mass temperature was 560C. One and a quarter hours after the diphenyl oxide feed was initiated, all of the diphenyl oxide had been added and the reaction mass temperature was 570C. The compressor on the refrigeration system was shut off to allow slow warm-up of the condenser. The reaction mass was refluxed through the fractionation column. At one hour and 18 minutes after feed initiation, the reaction mass temperature was 590C. Two hours and three minutes after diphenyl oxide feed initiation the condenser water was at 2O0C and the reaction temperature was at 610C. At two hours and seven minutes after feed initiation, the condenser water was at 3O0C. Thirty two minutes later the addition funnel was replaced with a N2 inlet. A slow N2 purge of the reactor was started. The reaction mass temperature was 610C. The N2 purge was at 100 mL/min into the vapor space of the reactor. Four hours and fifty minutes after the initiation of the diphenyl oxide feed, the reaction mass temperature was 610C and the condenser water was at 370C. At six hours and 15 minutes after the initiation of the diphenyl oxide feed the reaction mass was cooled to 550C, 350 mL deionized H2O was added, the fractionation column was removed, and the reactor was set for distillation. Br2 was distilled off. When most of the Br2 was gone 150 mL more deionized water was added. The remaining Br2 was distilled off to 1000C. The remaining mixture was cooled to 6O0C, and 30 mL of 25% NaOH was added to pH 13-14. The resultant mix was filtered and washed well with deionized water. A sample was subjected to GC analysis. The GC trace showed the product to contain 0.21% of the first nonabromodiphenyl oxide peak (deemed to be meta- and para-hydrogen isomers), 0.24% of the second nonabromodiphenyl oxide peak (deemed to be the ortho-hydrogen isomer) and 99.54% of decabromodiphenyl oxide. The sample was oven dried.

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; ALBEMARLE CORPORATION; WO2008/27776; (2008); A2;,
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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. 1516-96-7, name is 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C15H23BrO

In a 300 mL reactor sufficiently dried and purged with argon, 0.46 g (18.8 mmol) of magnesium pieces were charged and vigorously stirred for 30 minutes while heating under reduced pressure. After cooling to room temperature, a piece of iodine and 20 mL of tetrahydrofuran were charged and stirred. To this solution, J.Am. Chem. Soc. 2006, 128, 16486. A 30 mL dilute solution of 5.17 g (17.3 mmol) of 1-bromo-3,5-di-tert-butyl-4-methoxybenzene synthesized by the method described above was added dropwise (1.0 mL added)After that, the mixture was heated to reflux until the color of iodine disappeared with a drier, and after the start of the reaction, the remaining droplets were dropped), and after completion of the dropwise addition, the mixture was heated to reflux in an oil bath at 80 C. for 1 hour.The reaction solution was cooled to -78 C., 2.20 mL (19.8 mmol) of trimethoxyborane was slowly added, and stirring was continued for 19 hours while slowly returning to room temperature. An aqueous solution of 1.0 M hydrochloric acid was added, the solubles were extracted with di-iso-propyl ether, and the obtained fraction was washed with water and saturated brine and dried over anhydrous magnesium sulfate. After magnesium sulfate is filtered, the filtrate is evaporated to give a residue, which contains 3.38 g (15.0 mmol) of the compound (A-4a) obtained in Synthesis Example 4-1, tripotassium phosphate 7. 34 g (34.6 mmol), 0.03 g (0.15 mmol) of palladium acetate, 2-dicyclohexylphosphino-2 ‘, 6’-dimethoxybiphenyl (0.10 g (0.23 mmol) of S-Phos), 35 mL of tetrahydrofuran and 7 mL of distilled water were charged, and the mixture was heated under reflux for 2 hours in an oil bath. The reaction solution is cooled to room temperature, a saturated aqueous ammonium chloride solution is added, and the soluble matter is extracted with n-hexane and ethyl acetate to obtainThe fraction was washed with brine and dried over anhydrous magnesium sulfate. After magnesium sulfate is filtered, the filtrate is evaporated and the obtained residue is purified by silica gel column chromatography to obtain the desired product represented by the following formula (A-4b) (hereinafter referred to as compound (A-4b)) Is 5.44 g (yield 99%) were obtained.

According to the analysis of related databases, 1516-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsui Chemicals, Inc.; Prime Polymer Co., Ltd.; Tanaka, Yoichi; Harada, Yasuyuki; Tamura, Naoya; Hato, Ikki; Tsuchitani, Hiroko; (68 pag.)JP2019/59723; (2019); A;,
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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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H13BrO

Compound 38E: Methyl 1-[3-(benzyloxy)propyl]-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)- 1 /-/-pyrrole-2-carboxylate.A mixture of methyl 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrrole-2- carboxylate (Compound 38F, 600 mg, 2.39 mmol) and 1-bromo-3-benzyloxypropane (575 mg, 2.51 mmol) in DMF (2.19 mL) was charged with cesium carbonate (778 mg, 2.39 mmol). The reaction mixture was allowed to stir at 70 °C for 16 hrs. The reaction mixture was diluted with water and then extracted with EtOAc (2x). The organic layer was washed with water (2x), brine (1 x), dried over Na2S04, filtered, concentrated in vacuo and purified using a Teledyne ISCO Combiflash.(R). Rf system [0–> 4percent Ethanol in DCM] to afford 442mg of the title compound (46percent). 1H NMR (400 MHz, CD3OD) delta 7.26 – 7.37 (m, 5H), 7.25 (d, J = 1 .8 Hz, 1 H), 7.17 (d, J = 1.8 Hz, 1 H), 4.45 (s, 2H), 4.42 (t, J = 6.8 Hz, 2H), 3.78 (s, 3H), 3.38 (t, J = 5.9 Hz, 2H), 2.01 (t, J = 6.2 Hz, 2H), 1 .31 (s, 12H). MS (ESI): m/z 440.59 [M+H]+. UPLC: tR = 1.60 min (UPLC-TOF: polar_2 min).

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; OSI PHARMACEUTICALS, LLC; CREW, Andrew, P.; DONG, Hanqing; FERRARO, Caterina; SHERMAN, Dan; SIU, Kam, W.; WO2012/74951; (2012); 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. 452-08-4, name is 2-Bromo-4-fluoro-1-methoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 452-08-4

106 ml of 2.5 M butyllithium in hexane are added dropwise at -20 C. to a solution of 2-bromo-4-fluoro-1-methoxy-benzene (50 g) in 1 l of pentane, and stirred for 15 min at -10 C., then cooled to -30 C. Then trimethylborate (30 ml) is added, stirred 30 min at 0 C., cooled to -10 C., followed by the addition of a 32% peracetic solution (103 ml) over 45 min keeping the temperature to below -5 C. and stirring 30 min at 0 C. The mixture is cooled to -10 C., 150 ml of a saturated NaHSO3 solution are added, stirred 1 h at AT, then after adding water, neutralizing with 330 g of NaHCO3 and decanting the pentane, the aqueous layer is extracted with DCM. The organic layer is washed with sodium hydroxide, the aqueous layer is acidified with a concentrated HCl solution, extracted with DCM and the organic layer is dried over MgSO4, filtered and concentrated to dryness. 27.1 g of desired product are obtained.

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; CEREP; US2009/233910; (2009); A1;,
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Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, 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 18800-30-1, Computed Properties of C8H8Br2O

EXAMPLE 1 A mixture of 2.8 parts of 1-bromo-4-(2-bromoethoxy)benzene, 5 parts of cis-4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-3-H1,2,4-triazol-3-one, 0.7 parts of potassium hydroxide and 100 parts of dimethyl sulfoxide was stirred for 4 hours at room temperature. The reaction mixture was poured into water. The product was extracted with dichloromethane. The extract was subsequently washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel usinq a mixture of trichloromethane and methanol (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanone and 2,2′-oxybispropane. The product was filtered off and recrystallized from methylbenzene, yielding 5.2 parts (79%) of cis-2-[2-(4-bromophenoxy)ethyl]-4-[4-[ 4-[4-[[2-(2,4-dichlorophenyl)-2-(1 H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one; mp. 143.3 C. (compound 1).

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

Reference:
Patent; Janssen Pharmaceutica, N.V.; US4791111; (1988); A;,
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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 588-96-5 as follows. Recommanded Product: p-Bromophenetole

To a solution of 2R-allyl-3S-hydroxy-succinic acid diisopropylester (4.79 g, 18.5 MMOL), 4-bromo phenetole (3.19 ML, 22.2 mmol, 1.2 eq. ) and NEt3 (6.22 ML, 44.6 mmol, 2.4 eq. ) in CH3CN (40 ml), was added a sonicated (for 2 min) suspension of P (O-TOL) 3 (0.57 g, 2.22 mmol, 0.1 eq. ) and Pd (OAC) 2 (209 mg, 5%) in CH3CN (5 ML). The reaction mixture was heated to reflux for 2 hrs. CH3CN was removed under vacuo. The crude was extracted with AcOEt (3 X 200 ML), washed with water (50 ML) and with brine (50 ML). A purification by flash chromatography afforded the desired 2R- [3- (4-ETHOXY-PHENYL)-ALLYL]-3S- hydroxy-succinic acid diisopropyl ester (5.92 g, 84% yield).

According to the analysis of related databases, 588-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERNALIS (OXFORD) LIMITED; LABORATOIRES SERONO S.A.; WO2005/19194; (2005); A1;,
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Synthetic Route of 16618-68-1,Some common heterocyclic compound, 16618-68-1, name is 3-Bromo-5-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.

a)..Prep aration o f .intermediate 34; A solution of butanoyl chloride (0.0292 mol) in DCM (10ml) was added dropwise to a solution of 3-bromo-5-methyloxybenzenamine (0.0292 mol) and Et3N (0.035 mol) in DCM (50ml) at 5C under N2 flow. The mixture was stirred at room temperature for 1 hour. K2CO3 10% was added and the organic layer was decanted, dried (MgSO4), filtered off and evaporated till dryness, yielding 8 g (100%) of intermediate 34.

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/53373; (2009); A1;,
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