Tag: M.W=200-300

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. 3650-78-0, name is Methyl 3-(4-bromophenyl)acrylate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

820 mg (3.4 mmol) of methyl 4-bromocinnamate were dissolved in 7 ml of dry toluene, added with 116 mg (0.1 mmol) of Pd(PPh3J4, a solution of 374 mg (1.1 mmol) of 4- cyanobenzeneboronic acid in 2 ml of MeOH, 6.8 ml of 2M Na2CO3 in water, and refluxed 9 h. Addition of EtOAc, washing with water, then with brine, filtration and flash chromatography (Merck silicagel) with Hexane/EtOAc mixtures 9/1 gave 273 mg of methyl 3-(4-cyanobiphenylyl)acrylate, mp. 150-1520C.A solution of the above compound (270 mg, 1.02 mmol) and of 2-tetrahydropyranyl- O-hydroxylamine (117 mg, 1.02 mmol) in 14 ml THF was cooled at -780C, added with 1.07 ml of sodium hexamethyldisilazane, stirred 2 hrs, then heated at -2O0C, cooled again at – 780C, quenched with NH4CI, extracted with AcOEt, the extract evaporated and chromatographed (Merck silicagel) with Hexane/EtOAc 6/4 to give 189 mg of 2- EPO tetrahydropyranyloxyamide of 3-(4-cyanobiphenylyl)acrylic acid, as a white solid, mp. 211- 2130C.A solution of the above compound (187 mg, 0.54 mmol) in 5 ml of MeOH was treated with 30 mg (0.16 mmol) of p-toluenesulfonic acid, stirred 24 h at room temp, filtered and washed with MeOH, to give 96 mg of 3-(4-cyanobiphenylyl)acrylic acid hydroxyamide, mp. 212-2140C, Rf 0.3 (CH2CI2/MeOH 95/5), 1H NMR: (DMSO-d6): 6.54 (d, 1 H, -CH=, J = 15.3 Hz), 7.51 (d, 1 H, CH=, J = 15.3 Hz), 7.69 (d, 2H, 2Ar, J = 8.2 Hz), 7.82 (d, 2H, 2Ar, J = 8.2 Hz), 7.8-8.0 (m, 4H, 6Ar), 9.05 (s, 1 H, NH), 10.80 (s, 1 H, OH).

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; SIGMA-TAU INDUSTRIE FARMACEUTICHE RIUNITE S.P.A.; WO2007/383; (2007); A1;,
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Reference of 23877-12-5, These common heterocyclic compound, 23877-12-5, name is tert-Butyl 2-bromo-2-methylpropanoate, 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.

Production Example 10 Synthesis of tert-Butyl 2-[2-[2-[N-2-(4-chlorophenoxy)ethylaminocarbonyl]ethyl]phenoxy]-2-methylpropionate N-(4-Chlorophenoxyethyl)-3-(2-hydroxyphenyl)propanamide (11.6 g, 36.3 mmol) was dissolved in acetonitrile (15 mL), and potassium carbonate (15.0 g, 109 mmol) was added thereto. Subsequently, tert-butyl 2-bromoisobutyrate (20.2 g, 90.7 mmol) was added thereto, followed by stirring for 4 days at 70 C. Subsequently, water was added thereto, and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with brine, and the resultant mixture was subjected to drying over anhydrous sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (chloroform/methanol=50/1), whereby the target compound was obtained (7.4 g, 44%).

The synthetic route of 23877-12-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOWA CO., LTD.; US2005/101636; (2005); A1;,
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Related Products of 24807-40-7, 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. 24807-40-7 name is Methyl 3-(4-(benzyloxy)phenyl)propanoate, 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.

2 N Sodium hydroxide aqueous solution (3.5 mL) and water (10 mL) were added to a tetrahydrofuran-methanol solution (20 mL-10 mL) of the compound obtained in (1) (1.60 g), and stirred for 1 hour at 60C. The reaction solution was made acidic with 1 N hydrochloric acid, and then extracted with diethyl ether. The extract was washed with saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from diethyl ether-hexane to obtain 3-[4-(benzyloxy)phenyl] propionic acid (1.27 g) as colorless crystals. 1H-NMR (300MHz, CDCl3); delta 2.65 (2H, t, J=7.8Hz), 2.91 (2H, t, J=7.8Hz), 5.04 (2H, s), 6.91 (2H, d, J=8.7Hz), 7.13 (2H, d, J=8.7Hz), 7.29-7.45 (5H., m)

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1849465; (2007); A1;,
Ester – Wikipedia,
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Reference of 6279-86-3, 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. 6279-86-3, name is Triethyl methanetricarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example IEthyl 2,4-dihvdroxy-7,7-dimethyl-5-oxo-5,6,7,8-tetrahvdroquinoline-3-carboxylate10 g 3-Amino-5,5-dimethyl-2-cyclohexen-1-one and 25 g 2-Ethoxycarbonyl-malonic acid diethyl ester are combined and heated for 10 minutes at 210C (bath temperature).Thereafter the mixture is cooled to room temperature and triturated with diethylether. The crystalline precipitate is collected by filtration and dried in vacuo.Yield: 9,9 g (49 % of theory)Mass spectrometry (ESI+): m/z = 280 [M+H]+ Rf-value: 0,45 (silica gel, dichloromethane/methanol 9: 1)

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, Triethyl methanetricarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WAGNER, Holger; BERTA, Daniela; FUCHS, Klaus; GIOVANNINI, Riccardo; HAMPRECHT, Wolfgang; KONETZKI, Ingo; STREICHER, Ruediger; TRIESELMANN, Thomas; WO2012/110599; (2012); A1;,
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Application of 99548-54-6, A common heterocyclic compound, 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, molecular formula is C9H9BrO2, 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.

Compound I-1B (4.56 g, 20 mmol) was dissolved in anhydrous THF (100 mL).After cooling to 0 C, LAH (0.8 g, 20 mmol) was added in portions to maintain the internal temperature of the reaction solution less than 5 C. After the addition, the temperature was slowly raised to room temperature for 2 hours.TLC showed that after the reaction was over, it was re-cooled to 0 C, 0.8 ml of water was added dropwise, 0.8 ml of 15% NaOH and 2.4 ml of water were added, and after stirring, the mixture was stirred for 1 hour and filtered.The obtained filtrate was dried to give Compound I-1C (3.7 g, yellow solid).Yield: 92.4%.

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; Guangzhou Dankang Pharmaceutical Biological Co., Ltd.; Xu Yong; Huang Lu; Lin Dang; Hu Hai; (29 pag.)CN110092740; (2019); A;,
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Some common heterocyclic compound, 935273-86-2, name is Benzyl 3,3-difluorocyclobutanecarboxylate, molecular formula is C12H12F2O2, 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. category: esters-buliding-blocks

Benzyl 3,3-difluorocyclobutanecarboxylate (2-C) (0.84 g, 3.72 mmol) was dissolved in ethanol (40 ml), and approximately 20 mg of palladium on activated carbon was added. The mixture was stirred at room temperature under hydrogen atmosphere for 12 hours, and then filtered through a pad of Celite. The filtrates were concentrated and dried in vacuo to give 2-D. lH NMR (500 MHz, CDCI3): delta2.86-2.93 (4H, m), 3.02-3.04 (IH, m) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 935273-86-2, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2007/47625; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 653-92-9,Some common heterocyclic compound, 653-92-9, name is Methyl 2-bromo-4-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.

General procedure: Method A: A sealed tube was charged with compound 4a,b (0.93 mmol), 5a-e (0.93 mmol), 5 mol % of Pd(OAc)2, 10 mol % of Xantphos, 2 equiv of Cs2CO3 (1.86 mmol) and 10 mL of 1,4-dioxane. The mixture was degassed and backfilled with argon, the reaction vessel was sealed with a Teflon tap and heated at 100 C for 12 h. The reaction mixture was cooled to rt and concentrated in vacuo. The residue was dissolved in chloroform, washed with 10% citric acid solution, brine solution, dried over anhydrous Na2SO4 and concentrated. The crude compound was purified by flash column chromatography using 3-5% of MeOH/CHCl3 as an eluent to give the title cyclized compound.Method B: To a thick-well borosilicate glass vial (5 mL) was added compound 4a,b (0.23 mmol), compound 5a-e (0.23 mmol), 5 mol % of Pd(OAc)2, 10 mol % of Xantphos, 2 equiv Cs2CO3 (0.46 mmol) and 1,4-dioxane (2 mL). The mixture was degassed and the reaction vial was sealed and placed in the CEM-DISCOVER microwave reactor and irradiated at 100 C for 15 min. After cooled to rt, the product was isolated as above described in method A.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-bromo-4-fluorobenzoate, its application will become more common.

Reference:
Article; Sorra, Kumaraswamy; Mukkanti; Pusuluri, Srinivas; Tetrahedron; vol. 68; 7; (2012); p. 2001 – 2006;,
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 17100-63-9 as follows. Safety of Methyl 4-bromo-3-methoxybenzoate

A suspension of methyl 4-bromo-3-methoxybenzoate (2.5 g; 10.2 mmol; 1.00 eq.), 4-methyl-3- thiopheneboronic acid (Aldrich 542393; 1.59 g; 11.2 mmol; 1.1 eq.), potassium carbonate (7.05 g; 51 mmol; 5 eq.) and Pd(PPh3)4 (1.18 g; 1 mmol; 0.1 eq.) in toluene (12.5 ml_) and water (12.5 ml.) was refluxed for 5 hours. The reaction mixture was cooled down to room temperature and filtered through a pad of celite which was further washed with touene (200 ml_). The filtrate was concentrated in vacuo and the residue taken up in Ethyl acetate (400 ml_). The organic layer was washed with sat. aq. NaHCC>3 (100 ml_), water (100 ml_) and brine (100 ml_) then dried over magnesium sulfate and concentrated in vacuo. The residue (2.3 g; 8.77 mmol; 1 eq.) was taken up in EtOH (69 ml_), sodium hydroxide (5M; 5.26 ml 26.3 mmol; 3 eq.) was added and the reaction mixture was stirred at 6O0C for one hour. After concentration in vacuo, the residue was taken up in water (200 ml_) and the aqueous phase was washed with Ethyl acetate then acidified to pH 2 with cone. HCI. The solution was concentrated to ca. 100 ml_ and the precipitate filtered off and dried to afford the title compound (1.81 g, 71 %) as a brown solid. HPLC (Method A) : Rt 3.99 min (purity 97.4%). LC/MS : 246.9 (M-H)”.

According to the analysis of related databases, 17100-63-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43890; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate, A new synthetic method of this compound is introduced below., COA of Formula: C9H9BrO2

Dissolve NaH (140mg, 3.50mmol, 60mass%) under nitrogen protectionN,N-dimethylformamide (10 mL) was added to it under ice bathMethyl 2-(4-bromophenyl)acetate (200 mg, 0.87 mmol),After stirring for 30 min, iodomethane (0.33 mL, 5.2 mmol) was added.The reaction was allowed to warm to room temperature and stirred for 12 h.The reaction was quenched with water (20 mL), EtOAc (EtOAc)Wash with saturated brine (50 mL), dryThe title compound was obtained as a colorless oil (150 mg, 67%).

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Liu Xinchang; Huang Jianzhou; Zhang Yingjun; S ¡¤geerdeman; (267 pag.)CN109111451; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 2967-66-0, 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. 2967-66-0, name is Methyl 4-(trifluoromethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows.

Several other esters, whose structure and names are described in Table 3, were hydro genated under the conditions described above using preformed RuCl2(L-I). Isolated yield are given in Table 4.Table 3: Structure and names of substrates usedTable 4: Hydrogenation of esters using RuCl2(L-I) EPO Sub.: Substrate as described in Table 3.Conv.: Conversion (in %, analysed by GC after silylation) of ester to alcohol after 2h30min.Reaction conditions: Substrate (20 mmol), H2 gas (50 bars), RuCl2(L-I) 0.05 mol%,NaOMe 10 mol%, THF (14 mL) at 1000C during 2h 30min.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-(trifluoromethyl)benzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; FIRMENICH SA; WO2006/106484; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics