Month: May 2021

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. 69038-74-0, name is tert-Butyl 3-Bromobenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 69038-74-0

General procedure: To a mixture of boronic acid ester 10 (2.5 mmol) and aryl bromide (1 mmol) in DME (20 mL) were added dichlorobis(triphenylphosphine)palladium (0.05 mmol) and 2 M aqueous Na2CO3 (5 mL), then the mixture was refluxed for 4 h. The mixture was cooled to ambient temperature and diluted with AcOEt, then washed with water, brine, dried over sodium sulfate, and filtered. After the filtrate was concentrated, the crude material was purified by silica gel column chromatography to give compounds 12a-12f.

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:
Article; Sakamaki, Shigeki; Kawanishi, Eiji; Nomura, Sumihiro; Ishikawa, Tsutomu; Tetrahedron; vol. 68; 29; (2012); p. 5744 – 5753;,
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Related Products of 957205-72-0,Some common heterocyclic compound, 957205-72-0, name is Methyl 3-methyl-4-(trifluoromethyl)benzoate, molecular formula is C10H9F3O2, 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.

3-Methyl-4-trifluoromethylbenzoic acid methyl ester (0.20 g) was dissolved in THF (10 mL), and lithium borohydride (0.060 g) was added to the solution. The reaction mixture was refluxed with stirring for 3 hours and cooled to room temperature. 1N hydrochloric acid was added to the reaction mixture, followed by extraction thrice, each with ethyl acetate. The extracts were combined and washed with saturated brine, followed by drying over sodium sulfate. Insoluble matter was removed by filtration, and then the filtrate was concentrated. The residue was purified by silica gel column chromatography, whereby the title compound (0.16 g) was yielded. 1H-NMR (CDCl3) delta : 1.72(1H,t,J=5.9Hz), 2.48-2.50(3H,m), 4.73(2H,d,J=5.6Hz), 7.26-7.26(1H,m), 7.29(1H,s), 7.59(1H,d,J=7.8Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-methyl-4-(trifluoromethyl)benzoate, its application will become more common.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2017263; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 326-58-9, name is Benzo[d][1,3]dioxol-5-yl acetate, molecular formula is C9H8O4, 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. Computed Properties of C9H8O4

Acetic acid benzo[1,3]dioxol-5-yl ester 15 (2.51g, 13.93mmol) was dissolved in glacial acetic acid (5mL), then a solution of concentrated HNO3 1.1mL (70%, d=1.413, 1.09g, 17.27mmol) in glacial acetic acid (2mL) was added dropwise. The reaction mixture was stirred at rt for 4h, then was cooled at 0C. The yellow solid was filtrated, washed with cold water, air-dried, and used in the next step without further purification (2.95g, yield 94%). 1H NMR (300MHz, CDCl3) delta: 2.37 (s, 3H), 6.15 (s, 2H), 6.65 (s, 1H), 7.60 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 326-58-9, its application will become more common.

Reference:
Article; Brogi, Simone; Ramunno, Anna; Savi, Lida; Chemi, Giulia; Alfano, Gloria; Pecorelli, Alessandra; Pambianchi, Erika; Galatello, Paola; Compagnoni, Giulia; Focher, Federico; Biamonti, Giuseppe; Valacchi, Giuseppe; Butini, Stefania; Gemma, Sandra; Campiani, Giuseppe; Brindisi, Margherita; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 438 – 457;,
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Electric Literature of 18014-00-1, A common heterocyclic compound, 18014-00-1, name is Dimethyl 2,5-dibromoterephthalate, molecular formula is C10H8Br2O4, 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 1] A mixed liquid of methyl p-dibromoterephthalate (Compound 1)(9.86 g, 28 mmol) synthesised according to the method of a literature (), sodium 2-hexylthiophene-5-borate (Compound 2)(15.5 g, 61.6 mmol) synthesised according to the method of a literature (), PdCl2(dppf)·CH2Cl2 (1.83 g, 2.24 mmol), and toluene (1 L) was refluxed under a nitrogen atmosphere for 9 hours. After the reaction mixed liquid was allowed to cool to room temperature, water was added to the reaction mixed liquid and the reaction mixed liquid was subjected to extraction with chloroform. The obtained organic layer was dried with sodium sulfate, and filtered, and thereafter, the solvent was distilled out under reduced pressure. The obtained mixture was separated and refined by a silica gel column chromatography to obtain dimethyl 2,5-bis(5-hexyl-2-thienyl)terephthalate (Compound 3)(10.8 g, 20.5 mmol) in a yield of 73%. The physical properties of dimethyl 2,5-bis(5-hexyl-2-thienyl)terephthalate (Compound 3) were as follows. 1H-NMR (CDCl3, delta ppm): 7.61 (s, 2H), 7.06 (d, 2H), 6.86 (d, 2H), 3.76 (s, 6H), 2.82 (t, 4H), 1.63-1.80 (m, 4H), 1.28-1.45 (m, 12H), 0.90 (t, 6H)

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; Sumitomo Chemical Company, Limited; EP2248818; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2672-58-4, name is Trimethyl benzene-1,3,5-tricarboxylate, 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 2672-58-4, name: Trimethyl benzene-1,3,5-tricarboxylate

a solution of triphenylphosphine (577 mg, 2.2 mmol) in anhydrous THF (5 mL) was added diethyl azodicarboxylate (2.2 M in toluene, 791 muL, 1.7 mmol) dropwise at 0C. After stirred at 0C for 50 minutes, a solution of 1,3,5-tri(hydroxymethyl)benzene (269 mg, 1.6 mmol, prepared by reduction of trimethyl 1,3,5-benzenetricarboxylate with lithium aluminum hydride in THF, co-evaporated with dry benzene and dried on high vacuum for couple hours before use) and thioacetic acid (108 muL, 1.45 mmol) in dry THF (4 mL) was added dropwise. After 1 hour, the ice/water bath was removed and the reaction was stirred at room temperature for 15 hours. The solvents were removed by rotary evaporation in vacuo. The residue was purified by flash chromatography to give 5-acetylthiomethyl-1,3-bis(hydroxymethyl)-benzene as colorless solid (110 mg). 1H NMR (400 Hz, CDCl3): delta 7.13-6.99 (m, 3H), 4.45 (apt, J = 20.4 Hz, 4H), 3.98 (apt, J = 20.4 Hz, 4H), 3.73 (bs, 2H), 2.24 (apt, J = 20.4 Hz, 3H); MS (ESI): m/z 249.0 (M + Na)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Trimethyl benzene-1,3,5-tricarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Sanofi-Aventis; EP1813614; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 1070-64-0, name is Ethyl 6,8-dichlorooctanoate, 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. name: Ethyl 6,8-dichlorooctanoate

1, 100 g (0.4mol) racemic Ethyl 6, 8-Dichlorooctanoic acid (95% industrial grade) is prepared first, and then treated with an alkali hydrolysis process so as to obtain (+/-)-DCA 80 g, to be dissolved into 300 ml ethyl acetate, followed by 24 g (0.2 mol) S-(-)-alpha-phenethylamine, afterwards, gradually cooled down to a temperature range between 0-10 C., overnight, filtered, and ultimately obtain 30 g wet (+)DCA S-(-)-alpha-phenethylamine salt. Afterwards, a recrystallization process is followed, wherein the (+)DCA-S-(-)-alpha-phenethylamine salt is dissolved in the ethyl acetate, and acidified with diluted hydrochloric acid, and extracted by methylbenzene, and distilled at low temperature to remove solvent, finally obtain 18.8 g (+)-DCA, [alpha]D25+48-49.6 with a yield rate from 42% to 46%.

The synthetic route of Ethyl 6,8-dichlorooctanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Rally Biochemical Inc.; US2007/15926; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 14920-81-1, name is Methyl 2,6-dimethylbenzoate, 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. Computed Properties of C10H12O2

General procedure: To a flame-dried 250 mL round-bottom flask under argon wereadded 4 (8.02 g, 28.4 mmol, 1 equiv), TMEDA (8.71 mL, 58.2mmol, 2.05 equiv), and anhydrous n-hexane (28 mL). Theresulting solution was cooled in an ice bath and sec-butyllithium(1.4 M solution in cyclohexane, 42.0 mL, 58.2 mmol, 2.05equiv) was added dropwise. The ice bath was removed and thereaction mixture was stirred at room temperature for 4 h. Thereaction was cooled to -78 C and a solution of methyl 2,4,6-trimethylbenzoate (5.11 g, 28.7 mmol, 1.01 equiv) in anhydrousn-hexane (28 mL) was added slowly via cannula. After the addition,the mixture was allowed to slowly warm to room temperatureand stirred for 12 h. The reaction was quenched with water(25 mL) and the biphasic mixture was stirred vigorously for 30min. The mixture was diluted with Et2O (100 mL) and the layerswere separated. The organic layer was washed with water(2 × 150 mL) and brine (1 × 150 mL). The organic layer wastransferred to a 250 mL round-bottom flask equipped with astir bar. To the vigorously stirred solution was added conc. HCl(12 mL), resulting in a bright-yellow precipitate. The suspensionwas stirred vigorously for 30 min then diluted with water (150mL). The layers were separated and the organic layer wasextracted with water (3 × 150 mL or until the washings becomecolorless). To the combined aqueous layers was added solidNaBF4 (9.35 g, 85.2 mmol, 3 equiv), resulting in a bright-yellowprecipitate. The resulting suspension was extracted withdichloromethane (3 × 150 mL or until the washings become colorless).To the combined organic layers was added HBF4·Et2Ocomplex (3.46 mL, 28.4 mmol, 1 equiv). The solution wasswirled to achieve homogeneity then washed with water(1 × 100 mL) and aq. NaBF4 (1 M, 1 × 100 mL). The organic layerwas dried over solid NaBF4, filtered, and concentrated to dryness.The residue was purified by trituration with hexanes andfiltered. The solid was rinsed with n-pentane and dried in vacuoto give xanthylium 3 (10.6 g, 21.3 mmol, 75% yield) as a yelloworangesolid.

The synthetic route of Methyl 2,6-dimethylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; White, Alexander R.; Wang, Leifeng; Nicewicz, David A.; Synlett; vol. 30; 7; (2019); p. 827 – 832;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 6642-30-4, A common heterocyclic compound, 6642-30-4, name is Methyl methylcarbamate, molecular formula is C3H7NO2, 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 10 2-SEC BUTYLPHENYL N-METHYLCARBAMATE To a mixture of methyl N-methylcarbamate (0.89 g, 0.01 mole) and 2-sec butylphenol (1.5 g, 0.01 mole) in dichloroethane (10 ml), a solution of phosphorus tribromide (2.7 g, 0.01 mole) in dichloro-ethane (6 ml) was added and the mixture was refluxed for eight hours. It was then worked up and purified as described earlier to give 2-sec butylphenyl N-methylcarbamate of the formula (III).

The synthetic route of 6642-30-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Council of Scientific & Industrial Research; US5066819; (1991); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3195-24-2, name is Diethyl 2,2-diallylmalonate, 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 3195-24-2, Product Details of 3195-24-2

Example 6: Comparison of Standard Activity Tests of the Ruthenium tetrasubstituted NHC complex H6 (see Example 3f) to the Ruthenium gem di-substituted NHC complex H8 (see Example 3h) for Ring Closing Metathesis (RCM), Cross Metathesis (CM) and Ring-Opening Metathesis Polymerization (ROMP) reactions. [0098] Example 6a. RCM Reactions: All tests were performed according to the experimental procedure described by Ritter et al. (see Ritter, T.; Heji, A.; Wenzel, A.; Funk, T. W. ; Grubbs, R. H., Organometallics, 2006, 25, 5740.) See Figure 7a, 7b and 7c. CD2CI2, 300C C6D6, 60uC(%)EtO2C CO2Et EtO2C CO2Et Catalyst Ytefd catalyst (1 mo. %)1) solvent, temperature O HO 99% {30 mi?) v-_. – / H6 95% (2h) 98% (5 mm)R7 R8 H8 95% (4h) 95% (10 min) EtO2C CO2Et EtO2C CO2EtHO 6% (96h) 30% (24 min) catalyst (5 mol %) H6 95% (4h) 98% {20 min)3) X ^?~ h P=^r ssoollvveenntt,, t teemmppeerraattuurree y H O H8 no reaction 55% (31 h)R11 R12

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, Diethyl 2,2-diallylmalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MATERIA, INC.; CALIFORNIA INSTITUTE OF TECHNOLOGY; WO2009/126831; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 7515-17-5,Some common heterocyclic compound, 7515-17-5, name is Methyl 3-(4-methoxyphenyl)propiolate, molecular formula is C11H10O3, 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 2.2 3- (4-Methanesulfonvl-phenvl)-2- (4-methoxv-phenyl)-pyrazolof 1. 5-blpyridazine (i) 2-(4-Methoxy-phenyl)-pyrazolo[1,5-b]pyridazine-3-carboxylic acid methyl ester Diazabicyclo [5.4. 0] undec-7-ene (22.76mL, 2eq) was added dropwise to a solution of methyl 3- (4-methoxy-phenyl)-prop-2-ynoic acid’ (14. 46g, 76mM) and 1-aminopyridazinium iodide2 (2eq) in acetonitrile under nitrogen and stirred for 6h. Purification by chromatography on silica gel eluting with toluene, then toluene : ethyl acetate (9: 1) gave the title compound (2.76g) as a brown solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-(4-methoxyphenyl)propiolate, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/48999; (2005); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics