Tag: M.W=200-300

Reference of 15964-79-1, 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. 15964-79-1 name is Methyl 2-(3,4-dimethoxyphenyl)acetate, 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 1.0 L three-necked round-bottomed flask was added 50 mL of THF and the reaction mixture was cooled to -78 C. Butyl lithium (BuLi, 1.6 M, 14.4 mL, 23 mmol) was added dropwise keeping the temperature below -70 C. Acetonitrile (1.3 mL, 25 mmol) in 30 mL of THF was added dropwise to the flask amidst stirring and cooling. After 2 hours (h) of stirring, (3,4-dimethoxyphenyl)acetic acid methyl ester (2.3 g, 11 mmol) was added to the resulting white colloidal mixture in the flask. The reaction mixture was stirred for a further 2 h, followed by the addition of saturated ammonium chloride solution (NH4Cl, 75 mL) at -78 C. The organic layer was separated, dried with sodium sulfate (Na2SO4), filtered to remove the drying agent and evaporated to dryness to give the crude product. This crude product was purified by silica gel column chromatography, eluting with 30-70% ethyl acetate (EtOAc) in hexanes to yield 4-(3,4-dimethoxyphenyl)-3-oxo-butyronitrile in the form of a solidifying amber oil, 1.8 g (75%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-(3,4-dimethoxyphenyl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; Cole, Derek Cecil; Boschelli, Diane Harris; Wang, Yanong Daniel; Asselin, Magda; Joseph-McCarthy, Diane Marie; Prashad, Amarnauth Shastrie; Wissner, Allan; Dushin, Russell; Wu, Biqi; Tumey, Lawrence Nathan; Niu, Chuan S.; Chen, Joan; US2007/287708; (2007); A1;,
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Application of 1459-96-7, These common heterocyclic compound, 1459-96-7, name is Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate, 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.

Example 81 Bicyclo-[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester (IV) A mixture of Bicyclo[2.2.2]octane-1,4-dicarboxylic acid dimethyl ester (III, Example 80, 20.4 g, 89.5 mmol), barium hydroxide octahydrate (14 g, 44.7 mmol) in methanol (160 ml) and water (40 ml) is stirred at 20-25 C. for 18 hour. The mixture is diluted with water (600 ml) and extracted with hexane (150 ml*2). The aqueous mixture is acidified (6 N hydrochloric acid) to pH=1-2 and extracted with chloroform (150 ml*2). The combined chloroform extracts are concentrated. The residue is dissolved in toluene, filtered and concentrated to give the title compound, mp=169-173 C.

The synthetic route of 1459-96-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Biogen, Inc.; US6649600; (2003); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 62638-06-6, 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. 62638-06-6, name is Dimethyl cyclohexane-1,3-dicarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 25; l,3-Dicarbomethoxybicyclo[3.2.1]octane; A cooled (-67C) solution of dry diisopropylamine (ll.OmL, 78 mmol) in anhydrous THF (60mL) in a 3-neck 500mL round bottom flask equipped with magnetic stirring, addition funnel, and gas inlet/thermometer was treated via syringe with 2.4N n-butyllithium/hexane (30mL, 72 mmol) at a rate to keep the pot temperature <-50C, warmed to 0C for 5 minutes, then recooled (-67 C). l,3-Dimethyl-3,4,5,6-tetrahydro-2(lH)-pyrimidinone (DMPU, 36.3mL, 300 mmole, dried over molecular seives) was added dropwise so as to keep pot temp < -60 C, then a solution of dimethyl cyclohexane-l,3-dicarboxylate (12.01g, 60 mmol) in anhydrous THF (20mL) was likewise added dropwise. After lh at -67 C, a solution of l-bromo-2-chloroethane (12.05g, 84 mmol) in anhydrous THF (15mL) was added dropwise so as to keep pot temp <-50 C, and the mixture was warmed to room temperature over 1.5h and stirred at room temperature for 18h, then cooled on an ice bath and quenched with saturated aqueous ammonium chloride (50mL). The organic solvent was removed in vacuo and the aqueous residue was extracted with 9:1 hexane/ethyl acetate (150mL, lOOmL, 2X50mL). The combined organic extracts were washed with water (lOOmL), dried (MgS04), and concentrated in vacuo. The residue was dissolved in methylene chloride and passed through a pad of alumina in a 60mL fritted glass funnel (eluted with methylene chloride) to afford 15.36g (97% of theoretical) of a pale yellow oil which was essentially the desired intermediate with minor impurities.A solution of l-(2-chloroethyl)-l,3-dicarbomethoxycyclohexane (all of semi-purified from 60 mmol dimethyl cyclohexane-l,3-dicarboxylate) and DMPU (36.3mL, 300 mmol) in anhydrous THF (150mL) under nitrogen in a 500mL 3-neck flask equipped with magnetic stirring, addition funnel, and gas inlet/thermometer was cooled to -67C. Meanwhile, a cooled (-67C) solution of dry diisopropylamine (ll.OmL, 78 mmol) in anhydrous THF (75mL) under nitrogen was treated via syringe with 2.4N n-butyllithium/hexane (30mL, 72 mmol), the mixture was warmed to 0C for 5 min, then recooled (-67C). The LDA solution was cannulated in portions (~6) into the other solution at a rate to keep pot temperature <-60 C, then the mixture was stirred at -67 C for 30 min, warmed to room temperature over 1.5h, then stirred at room temperature for 18h,. cooled on an ice bath and quenched with saturated aqueous ammonium chloride (50mL). The organic solvent was removed in vacuo and the aqueous residue was extracted with 9:1 hexane/ethyl acetate (150mL, lOOmL, 2X50mL). The combined organic extracts were washed with water (lOOmL), dried (MgS04), and concentrated in vacuo. The residue was dissolved in methylene chloride and passed through a pad of alumina in a 60mL fritted glass funnel (eluted with methylene chloride) to afford crude subject material (9.52g) as a pale yellow oil. Chromatography on silica gel (~400cc) eluted with 40%, then 50% methylene chloride/hexane, then methylene chloride alone, then 10% ethyl acetate/methylene chloride afforded 8.32g (61% for two steps from dimethyl cyclohexane-l,3-dicarboxylate) purified subject material as a very pale yellow oil. [M+H]+=226.9. *H NMR (CDC13) 8 3.66 (s,6H), 2.20-2.30 (m,lH), 2.00-2.10 (m,2H), 1.70-1.80 (m,5H), 1.55-1.65 (m,4H). 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, Dimethyl cyclohexane-1,3-dicarboxylate, other downstream synthetic routes, hurry up and to see. Reference:
Patent; ROYALTY, Susan Marie; BURNS, James Ford; SCICINSKI, Jan Jozef; JAGDMANN, JR., Gunnar Erik; FOGLESONG, Robert James; GRIFFIN, Kellee Renee; DYAKONOV, Tatyana; MIDDLEMISS, David; WO2006/12395; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Ethyl 2-bromo-3-methylbutanoate

A solution of pyrazine-2-carbothioamide (1 g, 7.19 mmol) in ethanol (10 ml) was treated with ethyl 2-bromoisovalerate (2.25 g, 10.8 mmol), and pyridine (853 mg, 872 mul, 10.8 mmol) is combined to give a dark brown suspension. and heated to 100 C. for 6 hours in a sealed tube. The reaction mixture was cooled and concentrated to dryness under reduced pressure, and the resulting suspension is extracted with ethyl acetate (3*50 mL). The organic layers were combined, washed with saturated NaHCO3 (1*50 mL), saturated sodium chloride (2*20 mL). The organic layers were dried over MgSO4 and concentrated in vacuo to give 5-isopropyl-2-pyrazin-2-yl-thiazol-4-ol (260 mgs, 16%) which was used directly without further purification.

The synthetic route of 609-12-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Alam, Muzaffar; Du Bois, Daisy Joe; Hawley, Ronald Charles; Kennedy-Smith, Joshua; Minatti, Ana Elena; Palmer, Wylie Solang; Silva, Tania; Wilhelm, Robert Stephen; US2011/71150; (2011); A1;,
Ester – Wikipedia,
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Electric Literature of 10203-58-4, These common heterocyclic compound, 10203-58-4, name is Diethyl isobutylmalonate, 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.

2-lsobuty3malonic acid diethyl ester (40. Og, 0.185 rnol) in DMF (50mL) was added dropwise to a stirred suspension of sodium hydride (60% in mineral oil, 8.0g, 0.33 mol) in 200 mL DMF (200mL) over 20 rain, at 0C under nitrogen. The mixture was stirred for 0.5 h at room temperature, cooled to 0 C and l,2,4-trifluoro-5-nitro-benzene (30. Og, 169.5 mmol) in DMF (150mL) was added dropwise. The resulting reaction mixture was stirred at room temperature for 16b, poured into ice water (2 OOmL) and extracted with EtOAc (3×1 OOmL). The combined organic phases were washed with water (3×1 OOmL), brine (lOOmL) and dried (MgS04).Evaporation of solvent under reduced pressure ga ve a brown oil which was purified by column chromatography over silica gel (Fle tane-EtOAc, gradient) to give 57.0 g (90%) of 2-(2,5- difluoro-4-nitropheny3)-2-isobuty3malonic acid diethyl ester as yellow oil.3FI NMR (300 MHz,CDCI3/TMS): delta 7.87 (dd, J = 12.3, 6.0 Flz, 1H), 7.79 (dd, J = 10.1 , 6.4 Hz, 1 H), 4.30-4.18 (m, 4H), 2.27 (d, J = 5.8 Hz, 2H), 1.60-1.50 (m, i l l ). 1.26 (t, J = 7.1 Hz, 6H), 0.82 (d, J = 7.0 Hz, 6H);3C NMR (75 MHz, CDClv’TMS): delta 168.2, 155.1 (d, Ja= 252.3 Hz), 150.9 (d, CF = 263.2 Hz), 135.7, 135. L 120.0 (dd,2JCF= 26.0,1= 4.0 Hz), 113.0 (d,2JC¥= 29.0 Hz), 62.3, 43.1 , 24.9, 23.8, 13.8.

Statistics shows that Diethyl isobutylmalonate is playing an increasingly important role. we look forward to future research findings about 10203-58-4.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; KOENIG, Gerhard; BLAIN, Jean-francois; WO2013/106328; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 4131-74-2 as follows. HPLC of Formula: C8H14O4S

Methanol (360 kg) was added to a glass lining kettle, stirred and cooled. The kettle was cooled to 0-5C. Methylamine (180 kg) was introduced within a period of 3-4 hours. After the introduction, the mixture was stirred for 10 minutes while keeping warm. The resultant product was discharged and sealed for storage.; The compound of formula II prepared according to Example 2 and a reacting mother liquid comprising methylamine (35%) were continuously added to the reaction kettle K1 (50 L) from the bottom at a speed of 1 kg per minute and 3 kg per minute, respectively. The resultant product was cooled to the temperature of 0-8C with stirring. The reaction solution overflowing the upper part (5/6 of the total height) of the reaction kettle K1 flowed into the reaction kettle K2 (50 L) from the bottom. The resultant mixture was cooled to the temperature of 0-8C with stirring. The reaction solution overflowing the upper part (5/6 of the total height) of the reaction kettle K2 flowed into the kettles K3 and K4 in the same manner. The reaction solution overflowing the upper part (5/6 of the total height) of the reaction kettle K4 alternately flowed into the centrifuges N1 and N2 having a diameter of 300 mm at a flowing speed of 4 kg/minute for a solid-liquid separation. The mother liquid entered the reaction kettle P (50 L) (in which liquid methylamine was continuously added to the kettle from the bottom at a speed of 0.26 kg/minute). The resultant product was subsequently pumped into the reaction kettle K1. The solid entered the reaction kettles Q1 and Q2 (50 L). The resultant mixture was washed with approximately equal mass of methanol and was subjected to a solid-liquid separation via the centrifuges R1 and R2 (300 mm), respectively. The solid was dried and entered the storage tank T. The experiment was carried out for 20 hours to give 498 kg of the compound of formula V (98.5% via chromatography analysis).

According to the analysis of related databases, 4131-74-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing Tianqing Chemicals Co., Ltd.; EP2216331; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 773134-11-5,Some common heterocyclic compound, 773134-11-5, name is Methyl 4-bromo-2,6-difluorobenzoate, molecular formula is C8H5BrF2O2, 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 methyl 4-bromo-2,6-difluorobenzoate (22.5 g, 90 mmol) in N,N- dimethylformamide (100 mL) was added (2,4-dimethoxyphenyl)methanamine (16.49 g, 99 mmol) and K2C03 (18.58 g, 134 mmol) and the mixture was heated to 100 C and stirred overnight. The mixture was added to 50 mL water, extracted with ethyl acetate (30 mL x 3), dried over Na2S04 and evaporated to afford a brown oil. The oil was purified by column chromatography on silica gel (ethyl acetate/petroleum ether = 0 – 10%) affording methyl 4-bromo-2-((2,4-dimethoxybenzyl)amino)-6-fluorobenzoate (20 g, 45.2 mmol, 50 % yield) as a yellow solid. NMR (400 Hz, DMSO-d6 ) delta: ppm 7.85 (t, 1 H, J = 4.4 Hz), 7.16 (d, 1 H, J = 6.4 Hz), 6.755 (s, 1 H), 6.66 (d, 1 H, J = 8.8Hz), 6.60 (m, 1 H), 3.83 (s, 3 H), 3.81 (s, 3H), 4.13-3.94 (m, 3H), 3.48-3.50 (m, 1 H), 3.74 (s, 3H)

The synthetic route of 773134-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; JIN, Qi; POHLHAUS, Denise Teotico; SPLETSTOSER, Jared; (320 pag.)WO2017/98440; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 79669-50-4, 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. 79669-50-4, name is methyl 5-bromo-2-methyl-benzoate, This compound has unique chemical properties. The synthetic route is as follows.

Step 2 Compound 1251 B (1.219g, 5.32 mmol) was dissolved in CCI4 (30 mL). NBS (947 mg, 5.32 mmol) and benzoyl peroxide (66 mg, 0.27 mmol) was added. The solution was stirred at 850C for 2 hours. After cooling down, the solid was filtered and the organic layer was washed with water (10 mL). The organic layer was dried over Na2SO4, concentrated by rotary evaporator, dried under vacuum. The residue was then dissolved in NH3-MeOH (7N, 10 mL) and transferred into a 75 mL pressure bottle. The solution was stirred at 90 0C for over night. The product was purified by C18 chromatography (CH3CN/water: 5% to 90%, with addition of 0.1% HCO2H) to give compound 1251C (800mg, 71%).

The chemical industry reduces the impact on the environment during synthesis methyl 5-bromo-2-methyl-benzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SCHERING CORPORATION; WO2007/84451; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 46064-79-3, The chemical industry reduces the impact on the environment during synthesis 46064-79-3, name is Methyl 3-amino-4-bromobenzoate, I believe this compound will play a more active role in future production and life.

A mixture of methyl 2-hydroxy-5,5-dimethylcyclohex-1-enecarboxylate (26 g, 0.141 mol), methyl 3-amino-4-bromobenzoate (25 g, 0.109 mol), polyphosphoric acid (220 g) and dioxane (220 mL) was heated at 130 C. for 5 hours. After cooling, the mixture was diluted with water. The resulting precipitate was collected by filtration and dried. The solid was suspended in methanol (400 mL), and TMSCl (90 mL) was added. The mixture was stirred at reflux for 5 hours, concentrated and treated with water (80 mL), extracted with ethyl acetate (250 mL). The organic layer was separated, concentrated and recrystallized with methanol to afford desired compound (10.6 g, 27%).

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, Methyl 3-amino-4-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhou, Changyou; Ren, Bo; Wang, Hexiang; US2015/18356; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 849758-12-9,Some common heterocyclic compound, 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, molecular formula is C8H6BrFO2, 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 mixture of 4-bromo-3-fluoro-benzoic acid methyl ester (10 g, 43 mmol), bis(pinacolato)diboron (13.7 g, 54 mmol) and potassium acetate (12.7 g, 129 mmol) in dimethylsulfoxide (100 ml) was purged with argon, followed by addition of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (3.5 g, 4.3 mmol). The mixture was heated at 80 C. for 3 h. After this time the mixture was cooled to 25 C., washed with water, extracted with ethyl acetate and concentrated. The resulting black oil was redissolved in ethyl acetate:hexanes 1:2 and filtered through a short pad of silica gel (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company). The filterate was concentrated in vacuo to afford 3-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (12 g, 99%) as a solid which was used in the next step without further purification.

The synthetic route of 849758-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Berthel, Steven Joseph; Chen, Li; Corbett, Wendy Lea; Feng, LiChun; Haynes, Nancy-Ellen; Kester, Robert Francis; So, Sung-Sau; Tilley, Jefferson Wright; US2011/144105; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics