Tag: M.W=200-300

Electric Literature of 57486-69-8, These common heterocyclic compound, 57486-69-8, name is Methyl 2-(2-bromophenyl)acetate, 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.

[00123] Methyl 2-(2-bromophenyl)-3-oxobutanoate: A round bottom flask was charged with a magnetic stir bar and methyl 2- (2-bromophenyl) acetate (25 g, 109 mmol) and THF (50 mL). This solution was cooled to -78 C before drop wise addition of a 1M solution of LiHMDS in THF (218 ml, 218 mmol). The reaction was stirred for 30 min at -78 C before addition of l-(lH-imidazol-l-yl)ethanone (14.42 g, 131 mmol) as a solution in a mixture of THF:DMF (112 mL THF, 24 mL DMF). The solution was stirred for 1 h before quenching with sat’d aqueous NH4C1 (-250 mL) and diluting with EtOAc. The layers were separated and the aqueous phase was extracted with additional EtOAc (~2 x 250 mL). The combined organic extract was washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The crude residue was purified via silica gel chromatography using an eluent of ethyl acetate/hexanes (10: 1) to afford methyl 2-(2-bromophenyl)-3-oxobutanoate (32.5 g, 102 mmol, 93 % ield).

Statistics shows that Methyl 2-(2-bromophenyl)acetate is playing an increasingly important role. we look forward to future research findings about 57486-69-8.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; AUDIA, James, Edmund; DAKIN, Les, A.; DUPLESSIS, Martin; GEHLING, Victor, S.; HARMANGE, Jean-Christophe; NASVESCHUK, Christopher, G.; VASWANI, Rishi, G.; WO2015/23915; (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. 40546-94-9, name is 6-Methyl-4-phenylchroman-2-one, A new synthetic method of this compound is introduced below., Application In Synthesis of 6-Methyl-4-phenylchroman-2-one

EXAMPLE 1; Preparation of 3-(2-hydroxy-5-methylphenyl)-3-phenylpropanol (VIII) A basic aqueous solution of sodium borohydride prepared beforehand by dissolving 23.8 g (0.630 moles) of NaBH4 at ambient temperature in 170 ml of H2O and 3.5 ml of 30% wt./vol. NaOH was added dropwise to a suspension of 3,4-dihydro-6-methyl-4-phenyl-2H-benzopyran-2-one of the formula (II) (100 g, 0.420 moles) in isopropanol (200 ml). Once addition was complete, the temperature was adjusted to 60 C. and the course of the reaction was monitored by TLC (eluent: cyclohexane/acetone: 70/30) until the substrate had completely disappeared. After 5 h, the reaction mixture was cooled to ambient temperature and HCl (2N) was added until a final pH of 7.0 was obtained. Stirring was continued for 30 min at ambient temperature, then the resultant suspension was filtered through a Buchner filter. The filtered solution was concentrated under reduced pressure and the crude residue was crystallised from toluene (280 ml) to yield 87.4 g (yield 86%) of 3-(2-hydroxy-5-methylphenyl)-3-phenylpropanol (VIII) as a white solid.

The synthetic route of 40546-94-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEMI SPA; US2006/79716; (2006); A1;,
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Synthetic Route of 1000342-11-9, 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. 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Synthesis of methyl 5-bromo-3-(ethylamino)-2-methylbenzoate To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (1.0 g, 4.09 mmol) and acetaldehyde (180 mg, 4.09 mmol) in dichloroethane (10 mL), acetic acid (1.47 g, 24.58 mmol) was added and reaction stirred at room temperature for 30 minutes. Then sodium triacetoxyborohydride (2.6 g, 12.29 mmol) was added at 0 C., allowed to attain room temperature and stirring continued for 2 h. On completion, reaction mixture was diluted with dichloromethane, washed with water, saturated aqueous sodium bicarbonate solution and dried over sodium sulphate. Removal of the solvent under reduced pressure followed by column chromatographic purification afforded the desired compound (600 mg, 55%).

The synthetic route of Methyl 3-amino-5-bromo-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KUNTZ, KEVIN W.; CHESWORTH, RICHARD; DUNCAN, KENNETH W.; KEILHACK, HEIKE; WARHOLIC, NATALIE; KLAUS, CHRISTINE; ZHENG, WANJUN; SEKI, MASASHI; SHIROTORI, SYUJI; KAWANO, SATOSHI; US2012/264734; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 251458-15-8, name is Methyl 2-(3-bromophenyl)-2-methylpropanoate, belongs to esters-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 251458-15-8, Safety of Methyl 2-(3-bromophenyl)-2-methylpropanoate

Methyl 2-(3-bromophenyl)-2-methylpropanoate (Pharmabridge, Doylestown, Pa., USA (190 mg, 0.74 mmol), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (206 mg, 0.81 mmol), [1,1?-bis(diphenylphosphino)ferrocene] dichloropalladium(II), complex with dichloromethane (27 mg, 0.04 mmol) and potassium acetate (217 mg, 2.22 mmol) were placed in a screw cap vial and flushed with a vacuum and argon cycle three times. Anhydrous 1,4-dioxane (4 mL) was added under argon and the resulting mixture was heated to 80 C. for 19 h. The reaction mixture was cool to RT and was diluted with ethyl acetate (20 mL). Celite (1 g) was added and filtered through a pad of celite. Solvents were removed under reduced pressure to afford the title compound which was used directly in the subsequent reaction.

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Reference:
Patent; Gilead Sciences, Inc.; Selcia Limited; Aciro, Caroline; Dean, David Kenneth; Dunbar, Neil Andrew; Highton, Adrian John; Jansa, Petr; Karki, Kapil Kumar; Keats, Andrew John; Lazarides, Linos; Mackman, Richard L.; Pettit, Simon N.; Poullennec, Karine G.; Schrier, Adam James; Siegel, Dustin; Steadman, Victoria Alexandra; (169 pag.)US2017/190737; (2017); A1;,
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Application of 10203-58-4,Some common heterocyclic compound, 10203-58-4, name is Diethyl isobutylmalonate, molecular formula is C11H20O4, 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 stirred suspension of LiAlH4 (3.5 equiv.) in dry THF (1.0mL/mmol) under nitrogen atmosphere was slowly added a solution of the corresponding diethyl alkylpropanedioate (1 equiv.) in dry THF (1.0mL/mmol) at 0C. The reaction mixture was allowed to warm to rt and was then refluxed for 48h before being cooled to 0C. The reaction was quenched by careful addition of a saturated aqueous solution of NH4Cl until neutral or acidic pH. The precipitated aluminium salts were removed by filtration through a pad of Celite and washed with diethylether or a mixture of MeOH/CH2Cl2/Et2O 1:1:1. The organic phase of the filtrate was recovered, washed with water and brine, dried over MgSO4, filtered off and concentrated under reduced pressure to afford the corresponding crude product which was pure enough to be directly used in the next step.

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

Reference:
Article; Meguellati, Amel; Ahmed-Belkacem, Abdelhakim; Nurisso, Alessandra; Yi, Wei; Brillet, Rozenn; Berqouch, Nawel; Chavoutier, Laura; Fortune, Antoine; Pawlotsky, Jean-Michel; Boumendjel, Ahcene; Peuchmaur, Marine; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 217 – 229;,
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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. 35065-86-2, name is 3-Bromophenyl acetate, A new synthetic method of this compound is introduced below., Formula: C8H7BrO2

3-Bromophenol (5) (10.0 g, 58 mmol) was dissolved in pyridine(30 mL) under ice-bath and was stirred for 30 min. Acetic anhydride (8.3 mL, 88 mmol) was added dropwise into above mixture at the same temperature. The ice-bath was removed after dropping and the mixture was stirred for 2 h. Concentrated HCl and ice-water (300 mL) was added to neutralize pH to 7. The mixture was extracted with AcOEt (100 mL 3). The organic layer was collected and washed with brine and dried over Na2SO4. Filtration and concentration in vacuo afforded yellow oil. In a 250 mL round bottom flask, the obtained yellow oil (6.45 g, 30 mmol) and anhydrous AlCl3 (12.02 g, 90 mmol) was mixed at 160 C for three hours. Reaction mixture was poured into ice water and concentrated hydrochloric acid solution was added to break complex formed during reaction.The mixture was taken in AcOEt (50 mL 3). The organic layer was combined and washed with water and brine, and dried over Na2SO4. After filtration and concentration in vacuo, the residues was purified by silica gel flash chromatography (PE/AcOEt 30:1) give (6) (4.74 g, 73.5%) as white solid.

The synthetic route of 35065-86-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gao, Hongping; Su, Ping; Shi, Yaling; Shen, Xiuxiu; Zhang, Yanmin; Dong, Jinyun; Zhang, Jie; European Journal of Medicinal Chemistry; vol. 90; (2015); p. 232 – 240;,
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Electric Literature of 10203-58-4,Some common heterocyclic compound, 10203-58-4, name is Diethyl isobutylmalonate, molecular formula is C11H20O4, 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 solution of diethyl isobutylmalonate (50.0 g, 231 mmol) in anhydrous DMF (200 mL) cooled in an ice bath was added aH (60 %, 1 1.1 g, 277 mmol) in small portions. After the addition, the reaction mixture was stirred at 0C for 10 min and then at room temperature for 30 min. 5-Chloro-2-nirrobenzotrifluoride (47.3 g, 210 mmol) in anhydrous DMF (50 mL) was added dropwise and the mixture was stirred at room temperature for two days. The DMF was removed under high vacuum and the residue was diluted with ethyl acetate (400 mL). Water (400 mL) was added dropwise; ammonium chloride (25 g) was added and the layers were separated. The organic layer was washed with brine (400 mL), dried over sodium sulfate, and concentrated under reduced pressure to give a red-brown oil, which was purified by silica-gel flashchromatography eluting with heptane / ethyl acetate (12: 1) to give the desired product diethyl 2-isobutyl-2-(4-nilro-3-(trifiuoromethyl)phenyl)malonate (74.4 g, 87%) as a yellow oil:]H NMR (300 MHz, CDC13): delta 8.07 (s, 1 H), 7.94 (d, 2 H, J ——- 8.7 Hz), 7.88 (d, 2 I S . ./ 8.7 Hz), 4.25 (m, 4 H), 2.33 (d, 2 H, J= 6.6 Hz), 1.51 (m, 1 H), 1.26 (t, 6 H, J = 7.2 Hz), 0.84 (d, 6 H, J = 6.6 Hz);J 3C MR (75 MHz, CDC13): delta 169.23, 146.71 , 142.86, 132.94, 127.94 (q, J —— 5 Hz), 124.55, 123.12 (q, J —— 33 Hz), 121 .79 (q, J = 272Hz), 62.19, 65.59, 44.16, 24.66, 23.66, 13.89.

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

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; KOENIG, Gerhard; BLAIN, Jean-francois; WO2013/106328; (2013); A1;,
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Application of 20330-90-9, A common heterocyclic compound, 20330-90-9, name is Dimethyl 5-chloroisophthalate, molecular formula is C10H9ClO4, 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 3-chloro-5-(hydroxymethyl)benzoate To a solution of dimethyl 5-chloroisophthalate (10.0 g, 43.7 mmol, Astatech) in methanol (50 mL) and methylene chloride (50 mL) at 0 C. was added sodium borohydride (5.5 g, 140 mmol, Aldrich). The reaction was allowed to gradually reach room temperature and stir for 1 hour. Additional portions of sodium borohydride (0.50 g, 13 mmol) were added at 2 hours and 3 hours. The reaction mixture was cooled to 0 C. and the reaction was quenched with water. The layers were separated and the aqueous layer was extracted with three portions of DCM. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-25% EtOAc in hexanes. Yield: (4.51 g, 51%). 1H NMR (400 MHz, CDCl3) delta 7.92-7.90 (m, 1H), 7.90-7.88 (m, 1H), 7.57-7.55 (m, 1H), 4.73 (s, 2H), 3.92 (s, 3H); LCMS (M+H)+: 201.1203.1.

The synthetic route of 20330-90-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Rodgers, James D.; Shepard, Stacey; Wang, Haisheng; Shao, Lixin; US2015/175604; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3399-21-1, name is cis-Dimethyl cyclohexane-1,4-dicarboxylate, belongs to esters-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 3399-21-1, Application In Synthesis of cis-Dimethyl cyclohexane-1,4-dicarboxylate

REFERENCE EXAMPLE 6 Monomethyl cis-1,4-cyclohexanedicarboxylate In 35 ml of methanol was dissolved 3.46 g of dimethyl cis-1,4-cyclohexanedicarboxylate, and 17.3 ml of 1N aqueous sodium hydroxide solution was added thereto, and the resulting mixture was stirred at room temperature for 1.5 hours. The solvent was distilled off under reduced pressure and the obtained aqueous solution was washed with ethyl acetate. The pH of the mixture was adjusted to 1 with diluted hydrochloric acid under ice-cooling and the mixture was extracted with ethyl acetate. The extracts were washed with an aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a colorless crystalline solid. Isopropyl ether was added to the crystalline solid and the crystalline solid was collected by filtration to obtain 1.76 g of the desired compound as a pale yellow crystalline solid. m.p.: 91-93 C.; NMR spectrum (CDCl3 +d6 -DMSO) delta ppm: 1.60-2.00(8H,m), 2.42-2.52(2H,m), 3.67(3H,s)

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Reference:
Patent; Sankyo Company, Limited; US5843973; (1998); A;,
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These common heterocyclic compound, 88709-17-5, name is Ethyl 2-ethoxy-4-methylbenzoate, 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. COA of Formula: C12H16O3

Ethyl-2-ethoxy-4-methylbenzoate (3, 5 g, 24 mmol), freshly recrystallized N-bromosuccinimide (4.7 g, 26.4 mmol), ATBN (30 mg) were mixed in dry carbon tetrachloride (25 ml). Mixture was irradiated with light using 500 W lamp and was refluxed for 12 hr. Reaction mixture was cooled to room temperature and filtered to remove succinimide. Filtrate was washed with water fol lowed by brine wash, dried on anhydrous sodium sulfate and solvent was removed under vacuum. Residue solidifies on keeping. It was dissolved in petroleum.ether (10 ml) by refluxing. Solution was kept at room temperature for 6 hr. Product ethyl 4-bromomethyl-2-ethoxy-benzoate (4) crys tallized out as yellow crystals. Cooled in ice bath and filtered. Crystals were washed with ice-cold pet ether. Dried in air.

The synthetic route of Ethyl 2-ethoxy-4-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kalkote, Uttam R.; Gurjar, Mukund K.; Joshi, Shreerang V.; Kadam, Suresh M.; Naik, Sanjay J.; US2004/192955; (2004); A1;,
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