Category: 104197-14-0

Reference of 104197-14-0,Some common heterocyclic compound, 104197-14-0, name is 4-Bromo-2,6-difluoroanisole, molecular formula is C7H5BrF2O, 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 136 Preparation of 1-(3,5-Difluoro-4-methoxyphenyl)-2,2,2-trifluoroethanone Isopropyl magnesium chloride lithium chloride complex (22.0 mL, 28.02 mmol) was added dropwise to a stirred solution of 5-bromo-1,3-difluoro-2-methoxybenzene (5.0 g, 22.42 mmol) at -5 C. in THF (100 mL) and the reaction mixture was stirred at same temperature for 30 min. Methyl triflouroacetate (3.67 g, 28.69 mmol) was added dropwise and then the reaction mixture was stirred at ambient temperature for 2 h. A 2 N HCl solution (200 mL) was added to quench the reaction and then it was extracted with diethylether. The organic combinded layers were washed with brine dried (Na2SO4), filtered and concentrated to afford the title compound (5.4 g, crude) as a yellow liquid. The material was taken on to next step without further purification. 1H NMR (400 MHz, CDCl3) delta 7.68-7.60 (m, 2H), 4.19 (s, 3H); ESIMS m/z 240.1 ([M]+).

The synthetic route of 104197-14-0 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 104197-14-0, 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. 104197-14-0, name is 4-Bromo-2,6-difluoroanisole belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 14. 2-r3,5-difluoro-4-(methyloxy)phenylH,4,5,5-tetramethyl-1.3,2- dioxaborolane; A solution of 4-bromo-2,6-difluoroanisole (223mg, 1 mmole), bis(pinacaolato)diboron (275 mg, 1.09 mmole), [1 ,1 ‘-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (40 mg) and KOAc (300 mg) in 5 ml of dioxane was heated in the microwave at 150 for 20 minutes. The reaction was diluted with H2O and extracted with Et2O. The extracts were washed with H2O, dried and evaporated. The residue was chromatographed on a Florisil column, and the titled compound was eluted with Et20, 158 mg (58%). 1H NMR (400 MHz, CDCI3) delta 7.32 (d, J=8Hz, 2H), 4.05 (s, 3H), 1.35 (s, 12H).

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, 4-Bromo-2,6-difluoroanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/63167; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 104197-14-0, 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 104197-14-0 as follows.

To a 200 mL flask which had been sufficiently dried under argon atmosphere, 30 mL of anhydrous pentane and 22.1 g (0.10 mol) of 4-bromo-2,6,-difluoroanisole were added and the mixture was cooled to -78 C. in a dry ice/acetone bath. Dropped thereto over 50 minutes was 61.2 mL of 1.6 mol/L n-butyl lithium hexane solution and the thus obtained mixture was subsequently stirred for 5 hours at -78 C. Thereto dropped over 30 minutes was 24.5 mL of 1 mol/L boron trichloride/hexane solution and the thus obtained reaction solution was stirred for 5 hours at -20 C. To this reaction solution, 80 mL of water was slowly added to hydrolyze the reaction mixture and the formed crystals were collected, which were then washed with 80 mL of hexane and 80 mL of water to obtain 13.0 g of tetrakis(3,5-difluoro-4-methoxyphenyl) lithium borate having an HPLC purity of 98.8% (Yield: 90%). The thus obtained product was subjected to measurements by 1H-NMR (heavy methanol solvent) and MALDI TOF-MS to confirm that it was the desired product. (Measurement Results)(1H-NMR (shift; ppm: multiplicity: number of protons)(3.8: s: 12) (6.5-6.6: m: 8)(0177)MALDI TOF-MS (m/z)mass: 583.25 (Theoretical value: 583.27)

According to the analysis of related databases, 104197-14-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Adeka Corporation; Kimura, Kentaro; Fujita, Shohei; Tamachi, Tomoya; US8383862; (2013); B2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 104197-14-0, name is 4-Bromo-2,6-difluoroanisole, belongs to ethers-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 104197-14-0, Formula: C7H5BrF2O

Example 27; Dicyclopropylmethyl [9-(3,5-difluoro-4-methoxyphenyl)-2,8-dimethyl-9H-purin-6-yl]-amine Dicyclopropylmethyl-^, 8-dimethyl-9H-purin-6-yl)-amine (0.05Og , 0.194 mmol), 4-bromo-2,6- difluoroanisole (0.087g , 0.388 mmol), Copper(l) Iodide (0.055g , 0.291 mmol), Cesium carbonate (0.158g , 0.485 mmol) and 1 ,10-Phenanthroline (0.070 g , 0.388 mmol) was dissolved in 2.0 ml of anhydrous DMF in a microwave vial with a septum cap. It was degassed alternatively with vacuum and nitrogen 3 times and then heated at 13O0C overnight in an oil bath. The crude was partitioned between 2 ml of water and 3 x 2 ml of DCM through a phase separating cartridge. Combined organics were dried under reduced pressure to yield a dark liquid which was purified by flash column chromatography in the ISCO system with 12g silica cartridge and a gradient of 0 to 40% EtOAc in heptane with sample loading in DCM. Fractions bearing product were combined to yield a transparent oil which was further purified by preparative HPLC method c. Fractions combined to yield the title compound as a solid (6.4mg, 8%).1H NMR (400MHz, CDCI3) delta = 0.39-0.60 (m, 8H), 1.07 (m, 2H), 2.47 (s, 3H), 3.52 (s, 3H), 4.90 (s, 3H),6.99 (d, 2H).LCMS (System 4): 2.90 mins m/z (APCI) = 401 [MH+], m/z (ES) = 401 [MH+]

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,6-difluoroanisole, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER LIMITED; WO2009/144632; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 104197-14-0, 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. 104197-14-0 name is 4-Bromo-2,6-difluoroanisole, 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.

[0241] Step a: Lithium diisopropylamine solution in THF (1 M, 25 mL, 25 mmol) was added slowly to a solution of 5-bromo-1,3-difluoro-2-methoxybenzene (4.5 g, 20.2 mmol) in anhydrous THF (50 mL) under N2 and vigorously stirred at 78 C. The reaction mixture was stirred at 60 C for 1 h, followed by rapid addition of DMF (5 mL). The reaction mixture was stirred at the same temperature and allowed to warm to 50 C over 1 h. The reaction was poured into a mixture of ice (200 g), concentrated hydrochloric acid (20 mL) and MTBE (100 mL) and the mixture was stirred and allowed to warm up to room temperature over 2 h. The oranic layer was separated, washed with brine and dried over MgSO4. The solvent was removed under reduced pressure to give 6-bromo-2,4-difluoro-3-methoxybenzaldehyde . MS: (ES) m/z calculated for C8H6BrF2O2 [M + H]+ 250.9, found 250.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,6-difluoroanisole, and friends who are interested can also refer to it.

Reference:
Patent; CHEMOCENTRYX, INC.; FAN, Pingchen; LANGE, Christopher W.; LUI, Rebecca M.; MALATHONG, Viengkham; MALI, Venkat Reddy; PUNNA, Sreenivas; SINGH, Rajinder; TANAKA, Hiroko; ZENG, Yibin; ZHANG, Penglie; (284 pag.)WO2018/222598; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

104197-14-0, Adding some certain compound to certain chemical reactions, such as: 104197-14-0, name is 4-Bromo-2,6-difluoroanisole, 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 104197-14-0.

A mixture of 4-bromo-2,6-difluorophenyl methyl ether (5.Og), 1 ,1-dimethylethyl 1- piperazinecarboxylate (5.Og), 2-biphenylyl[bis(1 ,1-dimethylethyl)]phosphane (0.666g), palladium acetate (0.246g), sodium tert-butoxide (3.01 g) in toluene(30ml) was heated at 9O0C for 16 hours. After cooling ,The reaction mixture was diluted with diethyl ether, filtered through a pad of celite. Then concentrated in vacuo to give a black oil. The desired product was isolated by column chromatography on silica eluting with a gradient of 5 to 100% ethyl acetate in pentane. The title compound was obtained as a solid, (90% yield), LC/MS (ESI) Found 229 (M-BOC+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 104197-14-0.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/94842; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem