Tag: M.W=200-300

6279-86-3, These common heterocyclic compound, 6279-86-3, name is Triethyl methanetricarboxylate, 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.

10 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 210 C. (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)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 6279-86-3.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/46304; (2012); A1;,
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Some common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, molecular formula is C7H13BrO2, 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. 609-12-1

General procedure: Benzenesulfonamide (1.2mmol), ethyl alpha-bromophenylacetate or ethyl pheny-lacetate (2.4mmol), and toluene (4mL)werecombinedinasealedtubeequippedwith astirbar.Themixturewasstirredat50Cfor10min,TiCl4 (1.8 mmol) was added, andthereactionmixturewasheatedto115C.Afteravariableperiodoftimethe mixturewasdilutedwithH2O (10mL)toremovetheexcessofTiCl4, filtered,andextracted withAcOEt(3¡Á15mL). The combined organic layers were dried over anhydrous Na2SO4 and thesolventwasevaporatedinvacuo.Crudecompoundswere purified by flash column chromatography (silicagel;cyclohexane=AcOEt 8:2). 2-Bromo-N-[(4-methoxyphenyl)sulfonyl]-3-methylbutanamide (4c). Sticky oil, 59% yield; IR(KBr) 3564, 3236, 2970, 1906, 1722, 1596, 1499, 1443, 1346, 1265, 1165, 1087, 1023, 865, 834,559 cm-1; 1H NMR (CDCl3) d 0.94 (d, 3H, J 6.3Hz, CH3), 0.95 (d, 3H, J 6.6 Hz, CH3), 2.19(octuplet, 1H, J 6.6 Hz, CH3CHCH3), 3.87 (s, 3H, OCH3), 4.09 (d, 1H, J 6.6 Hz, CHBr), 6.99 (d,2H, J 9.0 Hz, CH Ar), 8.00 (d, 2H, J 9.6 Hz, CH Ar), 9.09 (broad s, 1H, NH); 13C NMR (CDCl3)d 18.9 and 20.2 (CH3), 32.4 (CH3CHCH3), 55.7 (OCH3), 58.0 (CHBr), 114.1 (CH Ar), 129.0 (CSAr), 130.9 (CH Ar), 164.1 (CH3OC Ar), 166.2 (CONH); Anal calcd for C12H16BrNO4S: C 41.15; H4.60; N 4.00; found C 41.22; H 4.59; N 4.02 %.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 609-12-1, its application will become more common.

Reference:
Article; Ammazzalorso, Alessandra; Tricca, Maria Luisa; Bruno, Isabella; De Filippis, Barbara; Di Matteo, Mauro; Fantacuzzi, Marialuigia; Giampietro, Letizia; Maccallini, Cristina; Mollica, Adriano; Amoroso, Rosa; Synthetic Communications; vol. 45; 22; (2015); p. 2546 – 2554;,
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Adding a certain compound to certain chemical reactions, such as: 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, 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 653-92-9, 653-92-9

General procedure: Method A:16,17 A two-necked round-bottomed flask equipped with a reflux condenser and a magnetic stir bar was charged with the 2-bromobenzoic acid (20mmol) and freshly distilled methanol (25mL). The solution was heated in a hot water bath, conc. H2SO4 (8mmol) was added slowly and the reaction mixture was refluxed for 24h. After cooling to room temperature around half of the amount of the solvent was removed in vacuo and the residue was partitioned between water (50mL) and diethyl ether (70mL). The organic layer was separated and washed with saturated NaHCO3 (2¡Á50mL), water (50mL) and brine (50mL), dried over anhydrous MgSO4 and the volatiles were removed under reduced pressure. The crude product thus obtained was purified by flash chromatography on silica gel to afford the alkyl-2-halobenzoate. (0023) In a two-necked round-bottomed flask equipped with a reflux condenser and a magnetic stir bar the alkyl 2-halobenzoate (22.5mmol) was dissolved in freshly distilled dry THF (30mL) under argon. The solution was cooled to 0C using an ice bath and NaH (60% in mineral oil, 15mmol) was added portionwise. After stirring for 15min a solution of the alkyl acetate (15mmol) in dry THF (30mL) was added dropwise to the reaction mixture at 0C. The mixture was warmed up, stirred at room temperature for 2h and heated under reflux for 24h. After cooling to room temperature around half of the amount of the solvent was removed in vacuo and the reaction mixture was diluted with toluene (50mL). The resulting mixture was washed with 2N HCl (50mL), saturated NH4Cl (50mL), dried over anhydrous MgSO4 and the volatiles were removed under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford the alkyl 3-(2?-halophenyl)-3-oxo-propanoate 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, Methyl 2-bromo-4-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Weischedel, Heike; Sudheendran, Kavitha; Mikhael, Alevtina; Conrad, Juergen; Frey, Wolfgang; Beifuss, Uwe; Tetrahedron; vol. 72; 24; (2016); p. 3454 – 3467;,
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A common heterocyclic compound, 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, molecular formula is C10H11BrO2, 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. 14062-25-0.

Example 46A(+/-)-Ethyl (4-bromophenyl)(cyclopentyl)acetate; Under an atmosphere of argon, 5.54 g (49.4 mmol) of potassium tert-butoxide were dissolved in 100 ml of DMF, and the mixture was cooled to 0 C. 10 g (41.1 mmol) of ethyl 4-bromophenylacetate, dissolved in 20 ml of DMF, were then added. The reaction mixture was stirred at 0 C. for 30 min, and 5.29 ml (49.4 mmol) of cyclopentyl bromide were then added dropwise. The mixture was stirred at 0-5 C. for 1 h and then added to water (1 litre) and extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated. This gave 12.41 g (97% of theory) of the title compound in the form of a yellowish oil.LC-MS (Method 5): Rt=1.44 min; m/z=311/313 (M+H)+.1H-NMR (400 MHz, DMSO-d6): delta [ppm]=0.89-1.04 (m, 1H), 1.05-1.69 (m, 9H), 1.72-1.86 (m, 1H), 2.34-2.48 (m, 1H), 3.37 (d, 1H), 3.92-4.17 (m, 2H), 7.24-7.37 (m, 2H), 7.44-7.57 (m, 2H).

The synthetic route of Ethyl 2-(4-bromophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/172448; (2012); A1;,
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The chemical industry reduces the impact on the environment during synthesis 1731-86-8, name is Methyl undecanoate, I believe this compound will play a more active role in future production and life. 1731-86-8

General procedure: The succinic Gemini surfactants, dl- and meso-2,3-bis(alkyl)succinic acids, were synthesized by the oxidative coupling of enolates of fatty acid esters with copper(II) bromide according to Quermann et al. [35] and subsequent deprotection of ester groups. Following is a typical synthesis of di-tert-butyl 2,3-bis(undecyl)succinate, 2e: first of all, tert-butyl tridecanoate 1e was prepared from tert-butanol, tridecanoic acid, dicyclohexyl carbodiimide (DCC) and DMAP (0.2 equiv) in toluene under stirring at room temperature. In a dry 100 mL flask equipped with a dropping funnel, septum inlet, and magnetic stirrer, a solution of 12.5 mL of lithium diisopropylamide (2.0 M in hexane/THF) and 30 mL of dry THF were added under nitrogen. Under cooling at -78 C, 25 mmol of 1e in 10 mL dry THF was added dropwise over a period of 30 min, and then the mixture was stirred for an additional 15 min. With vigorous stirring 5.0 g of anhydrous CuBr2 powder was added all at once to the solution. After stirring for 30 min, the reaction was quenched by adding 50 mL of 1 M HCl at this temperature, and the mixture was allowed to reach room temperature. After extracting twice with hexane (75 mL each), the combined organic layer was washed with water and dried over Na2SO4. By means of a short path vacuum distillation apparatus, both unreacted ester and alpha-bromo ester (5e) were distilled off (*160 C,1 mmHg). The residue was subjected to column chromatography on silica eluting with hexane/diethyl ether(20:1) to separate dl- (dl-2e) and meso-isomers (meso-2e) at the yields of 36 and 25 %, respectively. Other dl- and meso-isomers of 2a-2g were also prepared in a similar manner, and diastereomers (dl and meso) were separated by SiO2 chromatography.

The chemical industry reduces the impact on the environment during synthesis 1731-86-8. I believe this compound will play a more active role in future production and life.

Reference:
Article; Kawase, Tokuzo; Kagawa-Ohara, Maiko; Aisaka, Tsunetomo; Oida, Tatsuo; Journal of Surfactants and Detergents; vol. 18; 4; (2015); p. 615 – 627;,
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51760-21-5, A common compound: 51760-21-5, name is Dimethyl 5-bromoisophthalate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

PREPARATION 47 3-bromo-5-(methoxycarbonyl)benzoic acid To a solution of dimethyl 5-bromoisophthalate (2.80 g, 10.25mmols) in methanol (18.5 mL) was added a solution of potassium hydroxide (0.29 g, 5.13mmols) in 3.7 mL of water. The mixture was stirred overnight under reflux. The mixture was partitioned between water and ethyl ether. The aqueous phase was extracted twice with ether. The aqueous was then acidified to acid pH with 5N HCl and was extracted three times with ethyl ether. The combined organics were washed with brine and dried over sodium sulphate. Purification by chromatography (hexane 100% to ethyl acetate 100%) gave 0.700 g (2.70 mmol, 26%) of the title compound. HPLC/MS (10 min) retention time 5.79 min LRMS: m/z 259 (M-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, Dimethyl 5-bromoisophthalate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Almirall, S.A.; EP2394998; (2011); A1;,
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14062-25-0, Name is Ethyl 2-(4-bromophenyl)acetate, 14062-25-0, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

Example 26; 2-(4-Bromo-phenyl)-acrylic acid ethyl esterTo a solution of (4-bromo-phenyl)-acetic acid ethyl ester (972.4 mg, 4 mmol), paraformaldehyde (240 mg, 8 mmol), and Bu4NCl (22 mg, 0.08 mmol) in DMF (10 mL) was added K2CO3 (1.32 g, 9.6 mmol). This mixture was heated at 60 degrees Celsius for 2 h. Then the mixture was cooled and diluted with EtOAc (30 mL) and washed with water (20 mL¡Á3), brine, dried over Na2SO4, filtered and evaporated. The residue was purified by flash column chromatography on silica gel to give a white solid (0.74 g, 73%). MS: calc’d 255 (MH+), exp 255 (MH+).

Statistics shows that Ethyl 2-(4-bromophenyl)acetate is playing an increasingly important role. we look forward to future research findings about 14062-25-0.

Reference:
Patent; Liang, Chungen; Tang, Guozhi; Wong, Jason Christopher; Wu, Xihan; US2010/69328; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 792-74-5, name is Dimethyl [1,1′-biphenyl]-4,4′-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 792-74-5, 792-74-5

a) Preparation of 4,4′-bis (Hydroxy-Methyl) Biphenyl. 789mg (20.8 mmoles) of LiAlH4 in 150ml of anhydrous THF (tetrahydrofuran) are placed in a 2-litre flask which has a mechanical agitator, cooler, filler funnel and heating bath. A solution, heated to 50oC, of 7.5g (27.7 mmoles) of 4,4′-bis (methoxycarbonyl)biphenyl in 500ml of anhydrous THF is added dropwise, over a period of 1 hour, to the mixture, heated in an inert atmosphere to 50oC under agitation. After a further 30 minutes of agitation in a heating bath, the mixture is cooled to ambient temperature and the excess LiAlH4 is destroyed by the careful addition of 15ml of a THF/H2O (80:20) mixture. The reaction mixture is filtered on Septum G2, washing the precipitate with anydrous ethanol (3x100ml). The combined filtrate and washings are evaporated to dryness under vacuum with the heating bath at 40oC. The residue is then redissolved with 100ml of hot acetone (50oC), eliminating the insoluble residue by filtration, dried on anhydrous Na2SO4 and evaporated to dryness. 5.74g of 4,4′-bis (hydroxymethyl) biphenyl are obtained with a molar yield of 96.6percent.

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 [1,1′-biphenyl]-4,4′-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENIRICERCHE S.p.A.; EP469682; (1992); A1;,
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25542-62-5, 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. 25542-62-5, name is Ethyl 6-bromohexanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedeure: In a 250-mL round-bottom flask, 4-hydroxybenzaldehyde (5g, 41 mmol, 1eq.) and K2CO3( 14g,101 mmol, 2.5eq) were dissolved in anhydrous DMF (25 mL). Ethyl 6-bromohexanoate (13.7g, 61 mmol, 1.5 eq.) was slowly added to the solution under nitrogen atmosphere and refluxed for 2-4 h. Reaction was monitored by TLC. The solution was filtered over Celite 535, diluted with ethyl acetate (150 mL), and washed with brine (100 mLx2). The organic phase was dried over MgSO4, filtered, and concentrated. The crude product, a colorless oil (10.66 g, 40 mmol, 99%), was used without further purification.

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

Reference:
Article; Mitachi, Katsuhiko; Salinas, Yandira G.; Connelly, Michele; Jensen, Nicholas; Ling, Taotao; Rivas, Fatima; Bioorganic and Medicinal Chemistry Letters; vol. 22; 14; (2012); p. 4536 – 4539;,
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Some common heterocyclic compound, 51329-15-8, name is Methyl 3,5-dibromobenzoate, molecular formula is C8H6Br2O2, 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. 51329-15-8

Methyl 5-bromo-2′-chlorobiphenyl-3-carboxylate and methyl 2,2″-dichloro-1,1′:3′,1″-terphenyl-5′-carboxylate Under argon, 60 mg (0.05 mmol) of tetrakis(triphenylphosphine)palladium(0) were added to 300 mg (1.02 mmol) of methyl 3,5-dibromobenzoate in 6 ml of dioxane. The mixture was heated to 110 C., and 1.0 ml (2.00 mmol) of 2 M aqueous sodium carbonate solution and 239 mg (1.53 mmol) of 2-chlorophenylboronic acid, dissolved in 1 ml of dioxane, were added successively. The mixture was then stirred at 110 C. for 1 h. For work-up, the reaction mixture was allowed to cool to RT and diluted with 20 ml of ethyl acetate and 20 ml of water. After phase separation, the aqueous phase was extracted two more times with in each case 20 ml of ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was separated into the components by preparative HPLC [Method 19]. This gave 142 mg (43% of theory) of methyl 5-bromo-2′-chlorobiphenyl-3-carboxylate (Example 113A) and 166 mg (46% of theory) of methyl 2,2″-dichloro-1,1′:3′,1″-terphenyl-5′-carboxylate (Example 114A) as reaction products. Example 113A GC/MS [Method 20]: Rt=7.50 min; MS [ESIpos]: m/z=324 and 326 (M)+. Example 114A GC/MS [Method 20]: Rt=10.26 min; MS [ESIpos]: m/z=356 and 358 (M)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51329-15-8, its application will become more common.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Furstner, Chantal; Keldenich, Joerg; Delbeck, Martina; Kolkhof, Peter; Kretschmer, Axel; Pluschkell, Ingo; Pook, Elisabeth; Schmeck, Carsten; Trubel, Hubert; US2013/190330; (2013); A1;,
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