Category: 1516-96-7

These common heterocyclic compound, 1516-96-7, name is 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene, 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. Recommanded Product: 1516-96-7

A -78 C. solution of 5-bromo-1,3-di-tert-butyl-2-methoxybenzene (2.142 g; 7.158 mmol) in dry THF (15 mL) was treated with n-butyllithium (7.00 mL, 1.13M in hex, 7.88 mmol). The solution was stirred at -78 C. for 15 min, then treated with trimethylborate (976 muL; 8.59 mmol). The reaction was allowed to warm to ambient temperature and evaporated to a thick oil.

The synthetic route of 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Alan D.; Santini, Conrad; US2009/30012; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 1516-96-7, name is 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C15H23BrO

In a 300 mL reactor sufficiently dried and purged with argon, 0.46 g (18.8 mmol) of magnesium pieces were charged and vigorously stirred for 30 minutes while heating under reduced pressure. After cooling to room temperature, a piece of iodine and 20 mL of tetrahydrofuran were charged and stirred. To this solution, J.Am. Chem. Soc. 2006, 128, 16486. A 30 mL dilute solution of 5.17 g (17.3 mmol) of 1-bromo-3,5-di-tert-butyl-4-methoxybenzene synthesized by the method described above was added dropwise (1.0 mL added)After that, the mixture was heated to reflux until the color of iodine disappeared with a drier, and after the start of the reaction, the remaining droplets were dropped), and after completion of the dropwise addition, the mixture was heated to reflux in an oil bath at 80 C. for 1 hour.The reaction solution was cooled to -78 C., 2.20 mL (19.8 mmol) of trimethoxyborane was slowly added, and stirring was continued for 19 hours while slowly returning to room temperature. An aqueous solution of 1.0 M hydrochloric acid was added, the solubles were extracted with di-iso-propyl ether, and the obtained fraction was washed with water and saturated brine and dried over anhydrous magnesium sulfate. After magnesium sulfate is filtered, the filtrate is evaporated to give a residue, which contains 3.38 g (15.0 mmol) of the compound (A-4a) obtained in Synthesis Example 4-1, tripotassium phosphate 7. 34 g (34.6 mmol), 0.03 g (0.15 mmol) of palladium acetate, 2-dicyclohexylphosphino-2 ‘, 6’-dimethoxybiphenyl (0.10 g (0.23 mmol) of S-Phos), 35 mL of tetrahydrofuran and 7 mL of distilled water were charged, and the mixture was heated under reflux for 2 hours in an oil bath. The reaction solution is cooled to room temperature, a saturated aqueous ammonium chloride solution is added, and the soluble matter is extracted with n-hexane and ethyl acetate to obtainThe fraction was washed with brine and dried over anhydrous magnesium sulfate. After magnesium sulfate is filtered, the filtrate is evaporated and the obtained residue is purified by silica gel column chromatography to obtain the desired product represented by the following formula (A-4b) (hereinafter referred to as compound (A-4b)) Is 5.44 g (yield 99%) were obtained.

According to the analysis of related databases, 1516-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsui Chemicals, Inc.; Prime Polymer Co., Ltd.; Tanaka, Yoichi; Harada, Yasuyuki; Tamura, Naoya; Hato, Ikki; Tsuchitani, Hiroko; (68 pag.)JP2019/59723; (2019); A;,
Ether – Wikipedia,
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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 1516-96-7 as follows. name: 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene

To a 300 mL pressure bottle was added 5-bromo-1,3-di-tert-butyl-2-methoxybenzene (26 g, 87 mmol).Trimethyl ethynyl silicon (14.1 mL, 100 mmol), cuprous iodide (332 mg, 1.74 mmol),Triphenylphosphine palladium dichloride (611 mg, 0.87 mmol), triethylamine (60 mL),The mixture was reacted at 75 C for 12 h, cooled to room temperature, filtered and concentrated and applied directly to next.

According to the analysis of related databases, 1516-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Shi Shiliang; Cai Yuan; Yang Xintuo; Li Feng; (67 pag.)CN109776422; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 1516-96-7, name is 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene, 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. COA of Formula: C15H23BrO

Production Example 7 of Optically Active AminoalcoholA 300 mL round-bottom four-neck flask equipped with a Dimroth condenser with a nitrogen introducing tube attached thereto, a thermometer, a magnetic rotator and a dropping funnel was heated under reduced pressure, nitrogen was then introduced into the flask, pressure in the flask was returned to normal pressure, and the flask was cooled to room temperature. After 1.99 g of magnesium and a minor amount of iodine were added to the flask, a small amount of a solution obtained by mixing 25.30 g of 4-methoxy-3,5-di-tert-butylbromobenzene and 119.0 mL of dehydrated tetrahydrofuran was added dropwise. The flask was heated, and it was confirmed that the Grignard reaction was initiated. Thereafter, the remaining solution was added dropwise over 30 minutes. The resulting mixture was refluxed for 1.5 hours. After the resulting reaction mixture was cooled to -10 C., 1.45 g of L-alanine methyl ester hydrochloride was added. The temperature of the resulting mixture was raised to room temperature, and the mixture was further refluxed for 3 hours. The resulting reaction mixture was cooled to 0 to 5 C. To the reaction mixture were added dropwise 70.0 mL of an aqueous saturated ammonium chloride solution, and further 20.0 mL of water. The resulting mixture was stirred at 20 C. for 12 minutes. The resulting mixture was extracted with 70.0 mL of diethyl ether three times. The resulting organic layers were mixed, and dried with anhydrous sodium sulfate. After sodium sulfate was removed by filtration, the resulting filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/9830/70) to obtain 3.32 g of a pale yellow solid of (S)-2-amino-1,1-di(4-methoxy-3,5-di-tert-butylphenyl)-3-methyl-1-butanol.1H-NMR (300 MHz, CDCl3, TMS standard)delta (ppm): 7.49 (2H, s), 7.34 (2H, s), 4.01 (1H, m), 3.86 (1H, brs), 3.67 (3H, s), 3.66 (3H, s), 1.44 (18H, s), 1.42 (18H, s), 1.22 (2H, br.s), 0.94 (3H, d)13C-NMR (75 MHz, CDCl3, TMS standard)delta (ppm): 158.58, 158.29, 143.46, 142.94, 141.10, 139.19, 124.95, 124.84, 79.58, 64.76, 53, 42, 36.58, 36.50, 32.91, 21.75, 18.07

The synthetic route of 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Masumoto, Katsuhisa; Yoshikawa, Kouji; US2011/166372; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 1516-96-7, name is 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene, molecular formula is C15H23BrO, 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: 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene

Reference Example 3 Bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphine oxide Under argon atmosphere, a solution of magnesium (4.0 g, 0.95 equivalents) and a small amount of iodine in THF (50 mL) was stirred at room temperature for 1 hour. After 4-bromo-2,6-di-tert-butylanisole (52 g, 0.175 mol) synthesised in Reference Example 2 was added at 46C to 53C thereto, the mixture was stirred at 5C for 1 hour. Then, dimethyl phosphite (11.4 g, 0.52 equivalents) was added and the mixture was stirred at 5C for 1 hour. After water (50 mL) was added at 3C and toluene (50 mL) and 6M-HCl (20 mL) were then added, the mixture was stirred at room temperature for 30 minutes. The reaction solution was allowed to separate into layers. An organic layer was washed successively with water (20 mL), a 5% NaHCO3 aqueous solution (20 mL) and a 5% NaCl aqueous solution (20 mL), dried over anhydrous magnesium sulfate and then naturally filtered. The filtrate was concentrated under reduced pressure. The residue was recrystallized from heptane to obtain the title compound (11.6 g, pale yellowish white crystal). Yield 20.5%, mp. 166.1C. 1H-NMR (300 MHz, CDCl3, TMS) delta: 1.38 (s, 36H), 3.68 (s, 6H) 7.49 (s, 2H), 7.54 (s, 2H), 8.01 (d, 1H, J = 474.4 Hz).31P-NMR (121 MHz, CDCl3, 85%H3PO4) delta: 23.57 (dquint, J=474.1 Hz, 14.0 Hz). Elementary analysis for C30H47O3P Calculated value; C: 74.04, H: 9.73, P: 6.36 Found value; C: 74.13, H: 9.93, P: 6.20.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1516-96-7, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1568701; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 1516-96-7, 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. 1516-96-7, name is 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

Under nitrogen protection, to a 250 mL dry 3-necked round bottom flask equipped with a magnetic stirrer and thermometer was added:THE was added dropwise to the solution of the residue prepared above under nitrogen at 0C. After stirring another 1.5h at room temperature, the mixture was quenched withwater at 0C and extracted three times withdichloromethane. The combined organic layers were dried over Na2504 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with petroleum ether/ethyl acetate = 75:25, to give product as a white solid (1.94 g, 81% yield).1.0 g tetraethyl (((2R)-propane-1,2-diylbis(oxy))bis(3,1-phenylene))bis(phosphonate) (2.0 mmol, 1.0 equiv.) in3.0 mL thionyl chloride (40.0 mmol, 20.0 equiv.) under nitrogen was added30.0 iL dimethylformamide (0.4 mmol, 0.2 equiv). The mixture was stirred under reflux for 18 h, during which time15.0 iL dimethylformamide (all together 8.0 mmol, 0.3 equiv.) was added after 12h. After the solvent was evaporated, the residue was dissolve in5.0 mL THE and concentrated in vacuo (once). The residue was used for the next step without further purification.To a phenyl magnesium bromide solution prepared from a suspension of0.53g magnesium turning (22.0 mmol, 11.0 equiv.) and6.0 g 5-bromo-1,3-di-tert-butyl-2-methoxybenzene (20.0 mmol, 10.0 equiv.) in20.0 mL10.0 mL50 mL

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DSM IP ASSETS B.V.; BONRATH, Werner; FENG, Zheng-Chuan; MEDLOCK, Jonathan, Alan; PENG, Kun; ZHU, Zhibin; (28 pag.)WO2018/189107; (2018); A1;,
Ether – Wikipedia,
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