Esters-buliding-blocks

Reference of 6091-64-1, These common heterocyclic compound, 6091-64-1, name is Ethyl 2-bromobenzoate, 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.

To a tube was added Hphosphinate 3a (173 mg, 1 mmol, 1 equiv), Pd(OAc)2 (4.5 mg, 0.02 mmol, 2 mol %), xantphos (12.7 mg, 0.022 mmol, 2.2 mol %), toluene and 1,2-dimethoxyethane (4.5 ml : 0.5 ml), i-Pr2NEt (0.23 ml, 1.3 mmol, 1.3 equiv) and ethyl-2-bromobenzoate (0.24 mL, 1.5 mmol, 1.5 equiv). The homogeneous mixture was stirred under a flow of N2 for 10 minutes and then heated at 115C for 24 hrs. The solvent was then evaporated and the resulting residue partitioned between EtOAc (10 ml) and NaHCO3 (5 ml). The aqueous layer was extracted with EtOAc (3x). The organic layers were combined, dried over MgSO4 and concentrated under reduced pressure. The resulting oil was then purified by chromatography (silica gel, hexane/ EtOAc, 5:5) to give a yellow oil. Yield: 83% (232 mg); 1H NMR (CDCl3, 300 MHz) delta 8.04-8.11 (m, 1H), 7-77-7.81 (m, 1H), 7.59-7.64 (m, 2H), 4.41 (q, J = 7.0 Hz, 2H), 3.75-4.07 (dm, 2H), 1.90 (d, J = 15.2 Hz, 3H), 1.60-1.67 (m, 2H), 1.35-1.47 (m, 5H), 0.92 (t, J = 7.3 Hz, 3H) ppm; 13C NMR (CDCl3, 75.45 MHz) delta 168.1 (d, JPCCC = 3.4 Hz), 135.9 (d, JPCCC = 7.8 Hz), 133.9 (d, JPCCC = 8.1 Hz), 132.0 (d, JPCCCC = 2.3 Hz), 131.6 (d, JPC = 120.6 Hz), 131.0 (d, JPCC = 11.5 Hz), 129.7 (d, JPCC = 9.8 Hz), 64.5 (d, JPOC = 6.3 Hz), 61.9, 32.6 (d, JPOCC = 6.6 Hz), 18.9, 17.3 (d, JPC = 103.9 Hz), 14.2, 13.7 ppm; 31P NMR (CDCl3, 121.47 MHz) delta 43.07 ppm; HRMS (EI+) calcd for C14H21O4P 284.1177, found 284.1179.

Statistics shows that Ethyl 2-bromobenzoate is playing an increasingly important role. we look forward to future research findings about 6091-64-1.

Reference:
Article; Gavara, Laurent; Petit, Christelle; Montchamp, Jean-Luc; Tetrahedron Letters; vol. 53; 37; (2012); p. 5000 – 5003;,
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Adding a certain compound to certain chemical reactions, such as: 41658-03-1, name is Ethyl 3-bromopropiolate, 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 41658-03-1, COA of Formula: C5H5BrO2

General procedure: A solution of 3-phenyl sydnone (3, 100 mg, 1.0 equiv) in 4.0 mL p-xylene was added ethyl 3-bromopropynoate (120 mg, 1.05 equiv) and heated to reflux for 5 h. The residue was cooled down and added 2-aminophenylboronic acid pinacol ester (820 mg, 1.1 equiv), Pd(PPh3)4 (39 mg, 0.1 equiv), K2CO3 (2 mL, 2 M aqueous solution), and EtOH (4.0 mL). The reaction mixture was stirred at reflux for 24 h. When the reaction was completed, the reaction mixture was concentrated under reduced pressure to remove p-xylene and EtOH. The residue was added with 20 mL water, and extract with EtOAc (40 mL). The organic layer was filtered to remove the insoluble substances, then dried over MgSO4, filtered, and concentrated under reduced pressure. The residue solution was purified by column chromatography on silica gel to give the corresponding 2-arylpyrazolo[3,4-c]quinolin-4(5H)-one 1b-e and 2-arylpyrazolo[4,3-c]quinolin-4(5H)-one 2b-e products in 27-32% and 39-43% yields, respectively.

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

Reference:
Article; Chang, En-Chiuan; Wen, Ya-Lan; Chang, Chun-Hsi; Shen, Yun-Hwei; Wen, Shaw-Bing; Yeh, Mou-Yung; Wong, Fung Fuh; Tetrahedron; vol. 68; 29; (2012); p. 5920 – 5924;,
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Electric Literature of 142-91-6, 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. 142-91-6, name is Isopropyl palmitate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1.41 g of isopropyl palmitate (manufactured by Wako Pure Chemical Industries Ltd.), 1.00 g of phytosphingosine,and 14 mL of ethanol were added in a 30-mL eggplant flask and the mixture was stirred in a 55C hot water bath for 15min. After it was confirmed that the reaction system was homogeneous, 17.7 mg of potassium hydroxide (manufacturedby Kanto Chemical Co. , Inc.) was added. After 2 hours, a precipitate was confirmed and the mixture was continuouslystirred during a whole day and night. After the resulting reaction mixture was cooled to 30C, the precipitate was filteredand washed to obtain 1.45 g of N-hexadecanoyl-phytosphingosine in the form of a white solid in a yield of 82.9% (purity:95%).Melting point 114-117CIR (ATR, cm-1) 3336, 2917, 2849, 1611, 1542, 1468, 1076, 717MS (positive): [M + H]+ = 556.7, [M + Na]+ = 584.71H-NMR (deuterated pyridine, 500MHz, delta) 0.85 (3H, t, J = 7.0Hz), 0.85 (3H, t, J = 7.0Hz), 1.16-1.49 (46H, br), 1.69 (1H,m), 1.82 (2H, m), 1.94(2H, m), 2.24 (1H, m), 2.45 (2H, t, J = 7.6Hz), 4.29 (1H, m), 4.40 (1H, ddd, J = 5.9, 5.9, 5.5Hz),4.49 (2H, m), 5.10 (1H, m), 6.19 (1H, d, J = 6.7Hz), 6.53 (1H, d, J=6.2Hz), 6.62 (1H, t, J=5.4Hz), 8.52 (1H, d, J=8.5Hz)

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, Isopropyl palmitate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kao Corporation; HASHIMOTO, Hiroshi; SUGAI, Yoshiya; EP2757090; (2014); A1;,
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Related Products of 18013-97-3, 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. 18013-97-3, name is Diethyl 2,5-dibromoterephthalate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2,5-Dibromo-terephthalic acid diethyl ester (20 g, 53 mmol), dibenzofuran- 1 -boronic acid (29 g, 137 mmol) and tripotassiumphosphate monohydrate (48.5 g, 160 mmol) were added to water/toluene/dioxane (1 :1 :1 , 0.5 L). The solution was saturated with argon. Palladium(ll)-acetate (1 18 mg, 0.5 mmol) and tri-o-tolyl-phosphine (480 mg, 1 .6 mmol) were added and the reaction mixture was refluxed for 16 hours. After cooling down to room temperature, toluene (500 mL) was added and the organic phase was washed with water (3 x 500 mL) and then concentrated under reduced pressure. The residue was purified by recrystallization from toluene/ethanol. Yield: 22.2 g (40 mol; 76 %).

The synthetic route of Diethyl 2,5-dibromoterephthalate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; LINGE, Rouven; RODRIGUEZ, Lara-Isabel; MEYER, Sebastian; HEIL, Holger; (112 pag.)WO2018/95888; (2018); A1;,
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Application of 14062-24-9, These common heterocyclic compound, 14062-24-9, name is Ethyl 4-chlorophenylacetate, 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.

General procedure: Sodium hydride (1.33 ml, 2.61 mmol) was added dropwise to a solution of phenyl acetonitrile (1.0 g, 8.5 mmol)) in anhydrous THF (30 mL), the mixture was stirred at R.T. for30 minutes, followed by adding a solution of ethyl 4-chlorobenzoate (1.78 g, 10.2 mmol) in anhydrous THF (30mL). The mixture was refluxed till the reaction was finished.The result mixture was quenched with water and extracted with ether. The aqueous layer was acidified with 10% HCl to filter out the white precipitation, which was recrystallized with ether to give a white solid. Yield: 76%-80%.

The synthetic route of 14062-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hu, Chunqi; Shen, Jianfeng; Du, Wenting; Letters in drug design and discovery; vol. 14; 2; (2017); p. 151 – 158;,
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These common heterocyclic compound, 1000342-11-9, name is Methyl 3-amino-5-bromo-2-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. Formula: C9H10BrNO2

Example 18:Methyl 5-bromo-2-methyl-3-((tetrahydro-2H-pyran-4-yl)amino)benzoateTo a solution of the compound of example 17 (15 g, 61.5 mmol) in DOE (100 ml) were added dihydro-2H-pyran-4(3H)-one (11.35 mL, 123 mmol) and acetic acid (21 .11 mL, 369 mmol) and stirred at RT for 2h. The reaction mass was cooled to 0 00 and sodium triacetoxyborohydride (39.1 g, 184 mmol), was addedlot wise in 1 h which was left to stir at RT for 16h. After completion of the reaction, water was added and extracted with ethyl acetate. The compound was adsorbed on silica and purified by column chromatography (silica gel, 10-80 % ethyl acetate in petroleum ether) to yield the title compound.Yield: 15.1 g (73.6 %); 1H NMR (DMSO-d6, 300 MHz): 66.97-6.93 (m, 2H),3.87-3.85 (m, 2H), 3.80 (5, 3H), 3.59-3.55 (m, 1H), 3.46-3.41 (m, 2H), 2.14 (5,3H), 1.84-1.82 (m, 2H), 1.56-1.53 (m, 2H);MS (ESl+): m/z 329.1 [M+H] HPLO Purity: 98.3 %.

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; PIRAMAL ENTERPRISES LIMITED; ROYCHOWDHURY, Abhijit; SHARMA, Rajiv; GUPTE, Amol; KANDRE, Shivaji; GADEKAR, Pradip, Keshavrao; CHAVAN, Sambhaji; JADHAV, Ravindra, Dnyandev; THAKRE, Gajanan, Amrutrao; BAJAJ, Komal; JANRAO, Ravindra, Ashok; DEHADE, Amol; GAIKWAD, Nitin; KADAM, Kishorkumar; MORE, Tulsidas, Sitaram; GUHA, Tandra; SEELABOYINA, Balapadmasree; SABLE, Vikas, Vasant; WO2015/110999; (2015); A1;,
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Synthetic Route of 50893-36-2,Some common heterocyclic compound, 50893-36-2, name is 1-Chloroethyl ethyl carbonate, molecular formula is C5H9ClO3, 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 4 Preparation of ethyl N,N-di-n-butylcarbamate To a solution of 6.5 g (0.05 mole) of di-n-butylamine and 5.56 g (0.055 mole) of triethylamine in 40 ml of THF, 8.4 g (0.055 mole) of alpha-chloroethyl ethyl carbonate dissolved in 10 ml of THF are added dropwise and with stirring while the temperature is maintained at 5¡ã-10¡ã C. The mixture is allowed to return to room temperature, and is maintained with stirring at this temperature for 2 hours. After removal of the precipitate by filtration, evaporation of the solvent and distillation under reduced pressure, 6.3 g (63percent yield) of the expected carbamate are collected. B.p. 76¡ã C./26.6 Pa (0.2 mm Hg).

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

Reference:
Patent; Societe Nationale des Poudres et Explosifs; US4725680; (1988); A;,
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Electric Literature of 126430-46-4, These common heterocyclic compound, 126430-46-4, name is Benzyl 4-bromobutanoate, 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.

REFERENCE EXAMPLE 26 A mixture of benzyl 4-bromobutanoate (58.6 diethylamine (58.3 g) and dichloromethane (1000 ml) was stirred under reflux for 14 hours. The reaction mixture was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with ethyl acetate gave benzyl 4-(N,N-diethylamino)butanoate (33.8 g, 60%). NMR (delta ppm in CDCl3): 0.99 (6H,t,J=7.2 Hz), 1.78 (2H,quintet,J=7.2 Hz), 2.39 (2H,t,J=7.2 Hz), 2.49 (4H,q,J=7.2 Hz), 5.11 (2H,s), 7.30-7.41 (5H,m).

The synthetic route of 126430-46-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5650410; (1997); A;,
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Synthetic Route of 91-44-1, 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 91-44-1 as follows.

To a 50 mL round bottom flask containing acetonitrile (20 mL) was added 7-(diethylamino)-4-methylcoumarin (1.01 g, 4.37 mmol). Then N-bromosuccinimide (0.86 g, 4.8 mmol) was added in portions. After stirring at room temperature for 23 h, the reaction mixture was poured into water after the reaction was completed. The organic phase was extracted three times with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was removed by evaporation to give a yellow powder.

According to the analysis of related databases, 91-44-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sun Yat-sen University; Song Huacan; Cao Wenyan; Song Senchuan; Liu Jiarong; (18 pag.)CN109574942; (2019); A;,
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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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H16O3

Compound 300.1. Ethyl 4-methoxycyclohexanecarboxylate. Into a 100-mL round- bottom flask, was placed a solution of ethyl 4-hydroxycyclohexane-l-carboxylate (1 g, 5.81 mmol) in tetrahydrofuran (20 mL). Sodium hydride (349 mg, 8.72 mmol, 60percent) was added to the reaction at 0 ¡ãC in portions, then stirred for 20 min. This was followed by the addition of CH3I (865 mu, 11.6 mmol) at 0 ¡ãC. The reaction mixture was stirred overnight at room temperature, quenched with 6 mL of brine and extracted with 3 x 40 mL of ether. The combined organic layers were washed with 2 x 20 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 800 mg (74percent) of the title compound as a colorless oil.

According to the analysis of related databases, 3618-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; 3-V BIOSCIENCES, INC.; HEUER, Timothy Sean; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2015/95767; (2015); A1;,
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