Month: August 2021

Synthetic Route of 698-19-1, A common heterocyclic compound, 698-19-1, name is 1-(2-Bromophenyl)-N-methylmethanamine, molecular formula is C8H10BrN, 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.

SYNTHESIS EXAMPLE 2 Preparation of Compound 4 Compound 2 (1.486 g, 5.04 mmol), 2-bromo-N-methylbenzylamine (0.74 mL, 5.00 mmol) and triethylamine (1.40 mL, 10.0 mmol) were dissolved in anhydrous dimethylformamide (10 mL) and placed in a pressure bottle, under an N2 atmosphere. The reaction was heated to 130 C. for 2 days. The reaction was cooled to room temperature and diluted into deionized water (250 mL). The suspension was basified to pH>9 with 1 N NaOH, and extracted twice with ethyl acetate. The combined ethyl acetate extracts were dried over Na2SO4, filtered through a pad of silica gel (ethyl acetate), and dried under vacuum. The crude product was dissolved in ethyl acetate and minimal methanol and adhered to silica gel (25 g). The silica adhered compound was purified by flash silica gel chromatography (250 g silica, 3:1 hexanes:ethyl acetate) to yield 1.74 g (84%) of 4 as a white solid. ESI-MS m/z 414.1/416.1 [M+H]+. Analalysis: Calcd for C20H17BrFN3O: C, 57.98; H, 4.14; N, 10.14. Found: C, 58.08; H, 4.20; N, 10.02. 1H NMR (500 MHz, DMSO-d6) delta 10.06 (s, 1H), 8.69 (d, J=2.3 Hz, 1H), 8.09 (dd, J=9.0 Hz, 2.3 Hz, 1H), 7.77-7.74 (m, 2H), 7.68 (d, J=8.0 Hz, 1H), 7.33 (t, J=7.5 Hz, 1H), 7.22 (t, J=7.8 Hz, 1H), 7.18 (t, J=9.0 Hz, 2H), 6.99 (d, J=7.5 Hz, 1H), 6.78 (d, J=9.4 Hz, 1H), 4.89 (s, 2H), 3.20 (s, 3H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Syntrix Biosystems Inc.; US2012/46243; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 348-57-2, name is 1-Bromo-2,4-difluorobenzene, belongs to bromides-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 348-57-2, Product Details of 348-57-2

Under ice cooling, a solution of 25.35 g of 1-bromo-2,4-difluorobenzene in 100 mL of concentrated sulfuric acid was added with 25.7 g of N-bromosuccinimide, and stirred for 30 minutes at this temperature and for 2 days at room temperature. After cooling on ice, the reaction solution was added with ice, and extracted with 300 mL of diethyl ether. The organic layer was successively washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting crude product was purified and separated by silica gel column chromatography (n-hexane), to afford 34.6 g of the title compound as a colorless oil.1H-NMR ( 400 MHz, CDCl3 ) delta 6.99 ( 1H, t, J = 8.4 Hz ), 7.77 ( 1H, t, J = 6.8 Hz )

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, 1-Bromo-2,4-difluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai Co., Ltd.; EP1510516; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 2270-59-9, name is 5-Bromo-2-methylpent-2-ene, A new synthetic method of this compound is introduced below., Safety of 5-Bromo-2-methylpent-2-ene

Example 7 Synthesis of 2-hydroxy-N-methyl-N-[3-(4-methylpent-3-en-1-yl)-3-azabicyclo[3.2.1]oct-8-yl]-2,2-diphenylacetamide (Compound No. 15) Potassium carbonate (49 mg), potassium iodide (29.4 mg) and 5-bromo-2-methyl-2-pentene (35.3 muL) was added to a solution of Compound No. 12 (62 mg) in acetonitrile (3 mL). The mixture was stirred at 80 C. for 5 hours and subsequently at room temperature overnight. The mixture was concentrated under reduced pressure and the residue thus obtained was partitioned between dichloromethane and water. The separated organic layer was washed with water and brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue thus obtained was purified by preparative column chromatography to yield the title compound. Yield: 27 mg 1H NMR (CDCl3): delta 7.43-7.33 (10H, m), 5.07-5.04 (1H, m), 3.65-3.47 (1H, m), 3.15-2.05 (13H, m), 21.78-1.73 (6H, m), 1.33-1.1 (4H, m). Mass (m/z): 433 (M++1).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Kumar, Naresh; Kaur, Kirandeep; Gupta, Suman; Chugh, Anita; Salman, Mohammad; Shirumalla, Raj Kumar; Malhotra, Shivani; US2009/131410; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 2606-51-1,Some common heterocyclic compound, 2606-51-1, name is 5-(Bromomethyl)benzo[d][1,3]dioxole, molecular formula is C8H7BrO2, 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.

To a round-bottomed flask equipped with a reflux condenser and capped with a rubber septum were added (R)-6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline (2a) (0.6 mmol, 124 mg), potassium carbonate (1.2 mmol, 166 mg), anhydrous acetone (25 mL), and 5-(bromomethyl)benzo[d]-1,3-dioxole (3) (0.9 mmol, 194 mg). The mixture was refluxed under stirring and nitrogen atmosphere for 24 h. Afterwards, a saturated aqueous solution of NaCl (25 mL) was added to the mixture, which was extracted with CH2Cl2 (3 x 50 mL). The organic phase was dried over MgSO4. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using dichloromethane/ethyl acetate (1:1) as eluent, affording the desired product 1a. Yield: 174 mg (85%); [alpha]D20 = +18.6o (c = 0.05 g/100 mL CHCl3) ([alpha]D lit.13 = +18o (c = 0.05 g/100 mL CHCl3)); off-white solid; m.p. 120-121 oC; Rf = 0.35 (eluent: dichloromethane/ethyl acetate (1:1)); 1H NMR (300 MHz, CDCl3): delta 6.94 (s, 1H), 6.77 (q, J = 9.1 Hz, 2H), 6.55 (d, J = 11.5 Hz, 2H), 5.91 (s, 2H), 3.83-3.75 (m, 7H), 3.69 (d, J = 13.4 Hz, 1H), 3.59 (d, J = 13.4 Hz, 1H), 3.04 (ddd, J = 12.8, 8.4, 3.7 Hz, 1H), 2.81 (ddd, J = 15.4, 9.4, 5.7 Hz, 1H), 2.69 (dt, J = 12.0, 4.5 Hz, 1H), 2.57 (dt, J = 15.8, 3.9 Hz, 1H), 1.35 (d, J = 6.7 Hz, 3H); 13C NMR (75 MHz, CDCl3): delta 147.6, 147.2, 147.1, 146.3, 133.4, 132.1, 126.0, 121.5, 111.3, 110.3, 109.0, 107.7, 57.7, 55.8, 55.7, 55.5, 43.5, 26.6, 19.9; IR (KBr, cm-1) 2922.2, 2852.7, 1500.6, 1487.1, 1438.9, 1367.5, 1242.2, 1224.8; GC/MS (m/z, %): 341 (1.0), 135 (100.0), 326 (74.4), 327 (16.6).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-(Bromomethyl)benzo[d][1,3]dioxole, its application will become more common.

Reference:
Article; Correa, Bianca K.; Silva, Tamiris R.C.; Raminelli, Cristiano; Tetrahedron Letters; vol. 59; 39; (2018); p. 3583 – 3585;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 502496-36-8, name is 3-Bromo-5-fluoro-2-methylaniline, belongs to bromides-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 502496-36-8, Safety of 3-Bromo-5-fluoro-2-methylaniline

3-Bromo-5-fluoro-2-methylaniline (515 mg, 2.53 mmol) was dissolved in pyridine (20 ml). Then Intermediate 33 (547 mg, 2.53 mmol) and DMAP (3.09 mg, 0.025 mmol) were added and the resulting mixture was stirred at r.t. for 2 hrs. The solvents were removed in vacuo and the residue was taken up with EtOAc and H20. The organic layer was washed with sat. NaHC03 solution and brine, and then dried over Na2S04. The solvents were removed in vacuo and the resulting residue was recrystallized with MeOH to afford Intermediate 34 as colorless solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-5-fluoro-2-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; HENG, Richard; HOEGENAUER, Elizabeth, Kate; KOCH, Guido; PULZ, Robert, Alexander; VULPETTI, Anna; WAELCHLI, Rudolf; WO2013/8095; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 18599-22-9, name is 4-Bromo-3,3,4,4-tetrafluorobut-1-ene, 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. Quality Control of 4-Bromo-3,3,4,4-tetrafluorobut-1-ene

To a solution of 4-bromo-3,3,4,4-tetrafluoro-1-butene (4) (0.812g, 3.92mmol, 1.0 eq.) and 2,3-O-isopropylidene-d-glyceraldehyde (5) (2.16g, 9.40, 2.4 eq.) in THF (15.7mL) was added 1.06M MeLi/LiBr-free diethyl ether solution (8.86mL, 9.40mmol, 2.4 eq.) dropwise at -78C. The resulting mixture was stirred at the same temperature for 2h, and then quenched with saturated NH4Cl aq. The reaction mixture was extracted with Et2O three times. The combined extracts were dried over anhydrous Na2SO4, and the solvents were removed under reduced pressure. The residue was dissolved in EtOH. To this mixture was added an excess amount of NaBH4 at 0C. The resulting mixture was stirred at room temperature for several hours, and then quenched with sat. NH4Cl aq. The reaction mixture was extracted with EtOAc three times. The combined extracts were dried over anhydrous Na2SO4, and the solvents were removed under reduced pressure. The residue was chromatographed on a silica gel to give the corresponding alcohols, 6a (0.352g, 1.37mmol, 35% isolated yield, anti isomer) and 6b (0.402g, 1.58mmol, 40% isolated yield, syn isomer) as a colorless oil.

The synthetic route of 4-Bromo-3,3,4,4-tetrafluorobut-1-ene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Konno, Tsutomu; Hoshino, Tomoko; Kida, Takumi; Takano, Shinya; Ishihara, Takashi; Journal of Fluorine Chemistry; vol. 152; (2013); p. 106 – 113;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan, 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. Computed Properties of C18H11BrO

250 ml of four-mouth bottle, in an atmosphere of nitrogen, adding 16.2 g 4 – (4 – bromo – phenyl) dibenzofuran (0.05 muM) and 1.44 gMg powder (0.06 muM), 60 ml tetrahydrofuran, heating reflux for 4 hours, the reaction is complete, generating format reagent; 11. 1g10, 10 – dimethyl anthrone (0.05 muM) dissolved in 50 ml in tetrahydrofuran, dropping the above-mentioned form reagent, 60 °C reaction 24 hours, generating a large amount of white precipitate, finally adding saturated NHCl4 The format salt into alcohol; after the reaction, diethyl ether extraction, drying and steaming and, petroleum ether: methylene chloride mixed solvent (3:2) silica gel column purification, to obtain slightly yellow solid tertiary alcohol (yield is 85percent);

The synthetic route of 4-(4-Bromophenyl)dibenzo[b,d]furan has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CECEP Wanrun Co., Ltd.; Zhang Zhaochao; Wang Lichun; Li Chong; (29 pag.)CN107056737; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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 630-17-1 as follows. Safety of 1-Bromo-2,2-dimethylpropane

F) ((2′-fluoro-5′-methoxy-2-neopentyl-[1,1′-biphenyl]-4-yl)oxy)triisopropylsilane Under an argon atmosphere, a solution of 1-bromo-2,2-dimethylpropane (23.2 mL) in diethyl ether (250 mL) was added dropwise to magnesium (4.92 g) at a slow refluxing rate, and the reaction mixture was heated under reflux further for 30 min. Under an argon atmosphere, to a solution of 2′-fluoro-5′-methoxy-4-((triisopropylsilyl)oxy)-[1,1′-biphenyl]-2-yl trifluoromethanesulfonate (19.2 g) and a PEPPSI-SIPr catalyst (trade name) (1.26 g) in THF (200 mL) was added the solution prepared above, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound as a crude oil. This compound was used for the next step without further purification.

According to the analysis of related databases, 630-17-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; MIWATASHI, Seiji; SUZUKI, Hideo; OKAWA, Tomohiro; MIYAMOTO, Yasufumi; YAMASAKI, Takeshi; HITOMI, Yuko; HIRATA, Yasuhiro; SHIBUYA, Akito; EP2816023; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-(4-Bromophenyl)dibenzo[b,d]furan

Preparation of compound C-6-2 [135] After dissolving compound C-6-1 (17 g, 52.6 mmol) in THF (400 ml), and adding 2.5 M n-BuLi in hexane (31.5 ml, 78.9 mmol) to the reaction mixture in -78°C, the reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 12 hours with adding B(Oi-Pr) (24.1 ml, 105.2 mmol) slowly to the reaction mixture. After terminating the reaction, purified water 20 mL was dropped slowly to the reaction mixture. The reaction mixture was extracted with EA/NH4Cl aqueous solution. The obtained organic layer was concentrated, was triturated with MC/hexane, and then was filtered to obtain compound C-6-2 (14.5 g, 96 percent).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; AHN, Hee-choon; YOON, Seok-keun; KIM, Hee-sook; YANG, Soo-jin; LEE, Kyung-joo; KIM, Nam-kyun; CHO, Young-jun; KWON, Hyuck-joo; KIM, Bong-ok; WO2012/141499; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 50548-45-3, name is 1-Bromodibenzo[b,d]furan belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 50548-45-3

To a 500 ml round bottom flask in a nitrogen atmosphereCompound 1-Bromobenzofuran (10.0 g, 40.65 mmol),N- (4- (triphenylene-2-yl) phenyl) – [1,1′-biphenyl] -4- amine(N- (4- (triphenylen-2-yl) phenyl) – [1,1′-biphenyl] -4-amine)(17.75 g, 44.72 mmol)Xylene(Xylene) in 320 mlAfter complete dissolution, sodium tert-butoxide(sodium tert-butoxide) (5.08 g, 52.85 mol), And bis (tri-tert-butylphosphine) palladium (0)(Bis (tri-tert-butylphosphine) palladium (0))(0.21 g, 0.41 mmol), and the mixture was heated with stirring for 3 hours. After the temperature was lowered to room temperature, the salt was removed by filtrationXylene was concentrated under reduced pressure and recrystallized from 180 ml of tetrahydrofuran to obtain the above compound 5 (17.75 g, yield:68percent).

The synthetic route of 50548-45-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG CHEM, LTD.; KIM, Jin Joo; HONG, Sung gil; CHA, Yong bum; (27 pag.)KR2017/94665; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary