Category: 260806-90-4

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. 260806-90-4, name is Methyl 3-bromo-2-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Methyl 3-bromo-2-methoxybenzoate

2.4 g of lithium borohydride (LiBH4) was added to a solution of 5.3 g of 3-bromo-2-methoxy-benzoic acid methyl ester 5 in 200 mL of ether (Et2O) at 0 C. After stirring for 5 minutes, 5 mL of methanol was added. The reaction mixture was warmed to room temperature and kept there for 2.5 hours. Thereafter, 2.4 g more of lithium borohydride was added. The reaction mixture was quenched with aluminum chloride. After standard aqueous work up, and silica gel column purification (hexane/ethyl acetate 2:1), 4.0 g of 3-bromo-2-methoxy-phenyl-methanol 6 was obtained.

The synthetic route of 260806-90-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALLERGAN, INC.; US2009/306161; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

260806-90-4, name is Methyl 3-bromo-2-methoxybenzoate, 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. SDS of cas: 260806-90-4

Bis(dibenzylideneacetone)dipalladium(0) (11.5 mg, 2% mol) and 1,2,3,4,5-pentaphenyl-1-(di-tert-butylphosphino)ferrocene (29.1 mg, 1% mol) were added, under nitrogen flux, to a solution of 24 (500 mg, 2.04 mmol) in anhydrous toluene (5 ml), followed by K3PO4 (874 mg, 4.12 mmol) and n-butyl-boronic acid (251.8 mg, 2.47 mmol). The system was sealed, and the reaction mixture was stirred at 100 C for 19 h. After cooling to room temperature, toluene was removed by evaporation in vacuo to afford the crude product that was purified by flash column chromatography on silica gel (n-hexane/AcOEt 9:1) to give pure 25 (400 mg, yield: 88%). 1H NMR (200 MHz, CDCl3) delta (ppm): 0.93 (t, 3H, J = 7.3 Hz), 1.25-1.66 (m, 4H), 2.62-2.70 (m, 1H), 3.83 (s, 3H), 3.91 (s, 3H), 7.07 (t, 1H, J = 7.6 Hz), 7.35 (dd, 1H, J = 7.5 Hz, J = 1.8 Hz), 7.64 (dd, 1H, J = 7.5 Hz, J = 1.8 Hz); MS: m/z 222 (M+, 40), 223 ([M + 1]+, 100), 191 ([M – OCH3]+, 21).

The synthetic route of 260806-90-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bertini, Simone; Parkkari, Teija; Savinainen, Juha R.; Arena, Chiara; Saccomanni, Giuseppe; Saguto, Simone; Ligresti, Alessia; Allara, Marco; Bruno, Agostino; Marinelli, Luciana; Di Marzo, Vincenzo; Novellino, Ettore; Manera, Clementina; Macchia, Marco; European Journal of Medicinal Chemistry; vol. 90; (2015); p. 526 – 536;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 260806-90-4, 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. 260806-90-4 name is Methyl 3-bromo-2-methoxybenzoate, 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.

To a solution of methyl-3-bromo-2-methoxylbenzoate 6 (1.5 g, 6.12 mmol) in 13 mL of anhydrous 1,4-dioxane were subsequently added bis(pinacolate)diboron (2.3 g, 9.18 mmol), potassium acetate (1.5 g, 15.3 mmol), followed by bis(diphenylphospinoferrocene)palladium dichloride (134.6 mg, 0.184 mmol). The resulting mixture was heated to 110 C in an oil bath for 2 h or to 130 C in a microwave reactor for 30 min (5 bar, 200 W). Afterwards, the solvent was removed under reduced pressure to afford the crude pinacol ester that was used in the following step without further purification. Then, ammonium acetate (1.4 g, 18.36 mmol) and sodium periodate (3.9 g, 18.36 mmol) were added to a solution of the crude pinacol ester in a mixed solution of acetone (11.0 mL) and water (11.0 mL). The resulting mixture was stirred at r.t. until complete conversion of the starting material was observed by TLC. The precipitate was then filtered off, and the filtrate was concentrated under reduce pressure. The residue was extracted with ethyl acetate, and the combined organic extracts were dried over anhydrous Na2SO4, filtered and evaporated. The crude product was finally purified by silica gel column chromatography (n-hexane/ethyl acetate 6:4) to give 2-methoxy-3-(methoxycarbonyl)phenylboronic acid 7 (938.6 mg, 4.47 mmol). Yield: 73%. 1H NMR (400 MHz, CDCl3) delta (ppm): 8.04 (dd, 1H, J = 7.4 Hz, J = 1.9 Hz, H4), 7.96 (dd, 1H, J = 7.8 Hz, J = 1.9 Hz, H6), 7.24 (t, 1H, J = 7.5 Hz, H5), 6.15 (bs, 2H, B(OH)2), 3.94 (s, 3H, OCH3), 3.92 (s, 3H, COOCH3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-bromo-2-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Article; Bertini, Simone; Chicca, Andrea; Arena, Chiara; Chicca, Stefano; Saccomanni, Giuseppe; Gertsch, Juerg; Manera, Clementina; Macchia, Marco; European Journal of Medicinal Chemistry; vol. 116; (2016); p. 252 – 266;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 260806-90-4, name is Methyl 3-bromo-2-methoxybenzoate, molecular formula is C9H9BrO3, 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 C9H9BrO3

Methyl 3-bromo-2-raethoxybenzoate (1.9 g, 7.75 mmol, 1.0 eq) was dissolved in toluene and treated with 4-chloro phenyl boronic acid (1.2 g, 7.75 mmol, 1 eq). The reaction mixture was stirred for 10 minutes, purged with nitrogen for 10 minutes and degassed with vacuum. Tetrakis triphenylphosphine palladium (0.447 g, 0.387 mmol, 0.05 eq) and K2CO3 (1.6 g, 11.62 mmol, 1.5 eq) were then added to the mixture. The mixture was heated to reflux for 12 h at 120C and cooled to ambient temperature. The solvents were evaporated under reduced pressure and the reaction mass was diluted with water. The aqueous mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous Na?SC^ and concentrated under vacuum. The residue was purified by silica gel (60-120) column chromatography eluting with 5-10 % ethyl acetate/hexane as the eluent to afford the desired product (1.7 g, 80 %). 1H NMR (400 MHz, CDCl3) delta 3.49 (s, 3H), 3.93-3.95 (s, 3H), 7.20-7.25 (t, 1H), 7.39- 7.53 (m, 5H), 7.74-7.78 (t, 1H). MS (ESI): 277.1 (M + H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 260806-90-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/152082; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics