Category: 51329-15-8

Related Products of 51329-15-8, These common heterocyclic compound, 51329-15-8, name is Methyl 3,5-dibromobenzoate, 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.

Methyl 3,5-dibromobenzoate (294 mg, 1.0 mmol), 6-methoxy-1,2,3,4-tetrahydroquinoline (179 mg,1.1 mmol), BINAP (31 mg, 0.05 mmol) and palladium acetate (10 mg, 0.05 mmol) were added to 8 ml of toluene, Cs2CO3 (456 mg, 1.4 mmol) was added under nitrogen gas, heated to 100C and reacted for 12 h. A small amount of ethyl acetate was added, insoluble substance was removed by filtration, and the crude product was separated with silica gel column chromatography to obtain Compound 26, which was yellow oil, 255 mg, yield 77%. 1H NMR (CDCl3): delta ppm 1.96 (2H, m, 3′-CH2), 2.76 (2H, t, J = 6.4 Hz, 4′-CH2), 3.61 (2H, t, J = 6.0 Hz, 2′-CH2), 3.78 (3H, s, OCH3), 3.89 (3H, s, OCH3), 6.65 (1H, dd, J = 8.8 Hz and 3.2 Hz, ArH-7′), 6.68 (1 H, d, J = 2.8 Hz, ArH-5′), 6.95 (1 H, d, J = 9.2 Hz, ArH-8′), 7.43 (1 H, t, J = 2.0 Hz, ArH-4), 7.66 (1 H, t, J = 2.0 Hz and 1.6 Hz, ArH-6), 7.66 (1 H, dd, J = 1.2 Hz and 0.8 Hz, ArH-2). MS m/z (%) 376 (M+H+, 100), 378 (M+3+, 91).

Statistics shows that Methyl 3,5-dibromobenzoate is playing an increasingly important role. we look forward to future research findings about 51329-15-8.

Reference:
Patent; Institute Of Pharmacology And Toxicology Academy Of Militaty Medical Sciences P.L.A.; XIE, Lan; WANG, Xiaofeng; LEE, Kuo-Hsiung; EP2857393; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 51329-15-8, name is Methyl 3,5-dibromobenzoate, 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 51329-15-8, category: esters-buliding-blocks

a) 3-Bromo-5-hydroxy-benzoic acid methyl ester. A 5 mL tube was charged with 3,5-dibromo-benzoic acid methyl ester (586 mg, 2.0 mmol), bis(pinacolato)diboron (254 mg, 1.0 mmol), potassium acetate (294 mg, 3.0 mmol) and PdCl2(dppf) complex (50 mg). DMSO (3 mL) was added, and the solution was degassed with nitrogen, then the tube was sealed. After heating the tube for 16 h at 80 C., the mixture was diluted with ethyl acetate (10 mL) and extracted with brine (10 mL, three times), and saturated aqueous sodium bicarbonate (5 mL), and the organic layer was dried and concentrated to give 3-bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester. To a solution of this material in acetone (4 mL) was added an aqueous solution of Oxones (2 KHSO5.KHSO4.K2SO4) (1.23 g in 5 mL water), and the reaction mixture was stirred vigorously for 8 min at room temperature. The reaction mixture was quenched with aqueous sodium hydrogensulfite. The brown solution was extracted with ethyl acetate, and the organic layer was extracted with brine and water, dried and concentrated. The residue was passed through a short silica gel column using a gradient of methylene chloride to 2% methanol in methylene chloride as an eluent to give 104 mg of 3-bromo-5-hydroxy-benzoic acid methyl ester.

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

Reference:
Patent; Locus Pharmaceuticals, Inc.; US2008/280891; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

51329-15-8, name is Methyl 3,5-dibromobenzoate, 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. 51329-15-8

A mixture of compound 2 (5.6 g, 19.2 mmol), PMBSH (3.8 g, 24.7 mmol), Pd2(dba)3 (1.7 g, 1.9 mmol), Xantphos (2.2 g, 3.8 mmol) and DIPEA (4.9 g, 38.0 mmol) in 1,4-dioxane (100 mL) was heated to 100 C. for 16 h. The reaction mixture was concentrated under vacuum, and purified by column chromatography to give the compound 3 (3.9 g, 56%).

Statistics shows that 51329-15-8 is playing an increasingly important role. we look forward to future research findings about Methyl 3,5-dibromobenzoate.

Reference:
Patent; Novira Therapeutics, Inc.; Hartman, George D.; US2015/225355; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics