Category: 583-70-0

Electric Literature of 583-70-0, A common heterocyclic compound, 583-70-0, name is 2,4-Dimethylbromobenzene, molecular formula is C8H9Br, 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.

A dried round-bottom flask containing stir bar was charged with magnesium (530 mg, 21.70 mmol), small piece of iodine and dry THF (73 mL) was added under argon. Solution of 1-bromo-2,4-dimethylbenzene (3.65 g, 19.72 mmol) diluted in dry THF (3 mL) was added dropwise to the suspension and the solution was stirred at 50C for 60 mm. After the formation of Grignard reagent,_the_reaction_mixture_was_cooled_to_0C,_and_then_N-[(3-chlorophenyl)methylidene]-2-methylpropane-2-sulfinamide Ex.83a (3.37 g, 13.81 mmol) in dryTHF (3 mL)was added dropwise. The resulting mixture was stirred at rt. After the completion of the reaction, the reaction mixture was quenched with sat. NH4CI and the solution was extracted with EtOAc. The combined organic layers were washed with brine. After phases separation, the organic layer was dried over MgSO4, filtered and the solution was concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with a gradient of Hexanes/EtOAc from [90:10] to [60:40] to afford N-[(3-chlorophenyl)(2,4-dimethylphenyl)methyl]-2- methylpropane-2-sulfinamide Ex.83b (2.30 g, 48%) as yellow oil. 1 H NMR (400 MHz, DMSO-d6, din ppm): 1.11 (s, 9H), 2.22 (s, 3H), 2.26 (s, 3H), 5.67 (d, 1H, J=6.3Hz), 6.03 (d, 1H, J=6.3Hz), 6.98 (s, 1H), 7.04 (d, 1H, J=8.OHz), 7.19-7.27 (m, 1H), 7.26-7.40 (m, 4H).

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; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; (284 pag.)WO2018/138362; (2018); 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. 583-70-0, name is 2,4-Dimethylbromobenzene, A new synthetic method of this compound is introduced below., COA of Formula: C8H9Br

General procedure: A flask furnishedwith a dropping funnel was charged with the aryl/alkylbromide in Et2O. n-BuLi(1.6 M in hexane) diluted with Et2O was added dropwise at -78C. After addition, thereaction was kept at -78C for 10 min and was then allowed to warm to room temperatureand stirred for 30 min. The solution was transferred via cannula to SiCl4 dissolved in Et2Oat 0C. The reaction was stirred for 2 h and was allowed to warm to room temperature. Thesolvent was removed under reduced pressure and the residue dissolved in boiling toluene.Insoluble salts were removed via filtration through cellite and washed with hot toluene. Thesolvent from the resulting clear solution was removed under reduced pressure, followed bypurification via distillation or recrystallization.

The synthetic route of 583-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Binder, Judith; Fischer, Roland C.; Flock, Michaela; Torvisco, Ana; Uhlig, Frank; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 190; 11; (2015); p. 1980 – 1994;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 583-70-0, 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. 583-70-0, name is 2,4-Dimethylbromobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2: to a suspension of magnesium powder (239 mg, 9.79 mmol) in dry THF(small amount) was added dropwise 1 -bromo-2,4-dimethylbenzene (1.64 g, 8.86mmol) diluted in dry THF (20 mL) and the reaction was heated at 40C. Aftercompletion of Grignard reagent, 2-methyl-N-[(5-methylfuran-2-yl)methylidene]propane-2-sulfinamide (995 mg, 4.66 mmol) diluted in THF (10mL) was added to the solution. The reaction mixture was stirred at rt overnight.Water was added to quench the reaction. The two layers were partitionated andthe organic layer was dried over Mg504, filtered and the solution wasconcentrated under reduced pressure. The crude material was purified by silicagel column chromatography using a gradient of hexanes/EtOAc ([5:1] to [4:1]) to afford N-[(2,4-di methyl phenyl)(5-methylfuran-2-yl)methyl]-2-methylpropane-2- sulfinamide (1 .27 g, 85%) as yellowish oil

The synthetic route of 2,4-Dimethylbromobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; BONNET, Pascal; FOGHA, Jade; (82 pag.)WO2018/138354; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 583-70-0,Some common heterocyclic compound, 583-70-0, name is 2,4-Dimethylbromobenzene, molecular formula is C8H9Br, 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.

Add 2,4-dimethylbromobenzene to a 500 mL three-necked flask equipped with magnetic stirring at room temperature.2,4-Dimethylaniline, Pd2(dba)3, tri-tert-butylphosphine, sodium t-butoxide, toluene.After the addition, the nitrogen gas was replaced 3 times, the stirring was started, and the oil bath was heated and heated to reflux for 5 hours.The TLC tracking reaction showed that the two starting materials were completely reacted (PE/EA = 20:1, product Rf = 0.8) and the reaction was stopped. The reaction solution was cooled to room temperature, stirred for 10 minutes with pure water, separated, and the aqueous phase was extracted with toluene, and the toluene phase was combined and saturated.Washed with brine, dried over anhydrous sodium sulfate, filtered and evaporatedDilute the crude product with as little petroleum ether as possible: dichloromethane = 10:1, and place the liquid on a silica gel column.Keep the polarity of the eluent unchanged with petroleum ether: dichloromethane = 10:1 until the product is rinsed.Dry under reduced pressure to give an off-white solid.Recrystallization from n-hexane gave 13 g of a white crystalline solid.HPLC 99.18%, yield 57%.

The synthetic route of 583-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Gu’an Dingcai Technology Co., Ltd.; Gao Wenzheng; Ren Xueyan; (34 pag.)CN109665935; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 583-70-0, 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. 583-70-0, name is 2,4-Dimethylbromobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Examples 42-45 Bis-(2,4-dimethylphenyl)chlorophosphine (B42): A solution of 2.92 ml (2161 mmol) of 4-bromo-1,3-dimethylbenzene in 3 ml of Et2O were added at 0 C. to a suspension of 0.5 g (20.56 mmol) of magnesium turnings in 7 ml of THF and 7 ml of Et2O and also a crystal of iodine. The mixture was heated to room temperature, stirred further overnight and slowly added dropwise at 0 C. to a solution of 1.5 ml (10.31 mmol) of Et2NPCl2 in 8 ml of THF. The mixture was heated to room temperature and the solvent was subsequently removed under reduced pressure. After adding 60 ml of hexane, the mixture was filtered through Celite under argon and admixed with hydrogen chloride for 1 hour. After degassing, the resulting solids were filtered off under argon and dried. Yield: 1.4 g (58.3% of theory). 1H NMR (400 MHz, CDCl3) delta, 7.40 (d, Jmeta=4.5 Hz, 2H, arom.), 7.2 (m, 4H, arom.), 2.5 (d, JPH=2.0 Hz, 6H, CH3), 2.4 (s, 6H, CH3). 31P NMR (161.974 MHz, CDCl3) delta, 75.6.

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, 2,4-Dimethylbromobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Meseguer, Benjamin; Militzer, Hans-Christian; Castillon, Sergio; Claver, Carmen; Diaz, Yolanda; Aghmiz, Mohamed; Guiu, Ester; Aghmiz, Ali; Masdeu, Anna; US2005/80047; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

583-70-0, name is 2,4-Dimethylbromobenzene, belongs to bromides-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. HPLC of Formula: C8H9Br

To a suspension of Mg (1.32 g, 55 mmol) in THF (60 mL) was added a catalytic amount of and 1 -bromo-2,4-dimethylbenzene (0.50 g, 2.7 mmol). The reaction was initiated by heating and additional l-bromo-2,4-dimethylbenzene (8.75 g, 47.3 mmol) was added dropwise. The reaction mixture was stirred at rt for 4 h under N2. Benzonitrile (5.15 g, 50 mmol) was added dropwise to the Grignard system and the reaction mixture was stirred at rt for 16 h. The reaction was quenched by the addition of MeOH (20 mL), followed by portionwise addition of NaBH4 (1.9 g, 50 mmol). After stirring at rt for 5 h, the reaction was quenched by the addition of water (20 mL). Solvent was removed under reduced pressure. The residue was extracted with EtOAc (3 x 100 mL). The organic layer was washed with 1 N HC1 and the resultant precipitate was collected by filtration to afford the title compound (8.8 g, 84%) as a white solid. LC-MS-P1 : 195 [M- NH2]+; Rt: 1.232 min. lU NMR (500 MHz, DMSO-d6) delta ppm 9.15 (s, 2H), 7.55 (d, J= 8.0 Hz, IH), 7.45 – 7.32 (m, 5H), 7.12 (d, J= 8.0 Hz, IH), 7.04 (s, IH), 5.64 – 5.62 (m, IH), 2.27 (s, 3H), 2.22 (s, 3H).

The synthetic route of 583-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; BALOGLU, Erkan; BOHNERT, Gary, J.; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; SUNG, Leonard; WO2013/19682; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 583-70-0, 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 583-70-0 as follows.

According to Scheme 1 Step i: To a solution of 1-bromo-2,4-dimethyl-benzene (20.00 g, 108.07 mmol, 1.00 eq) in THF (100 mL) under N2 atmosphere and cooled to -70C, was added n-BuLi (2.5 M, 45.39 mL, 1.05 eq) dropwise. The reaction mixture was stirred at -70C for 2 hr. Then a solution of 1,4-dioxa-spiro[4.5]decan-8-one (17.72 g, 113.47 mmol, 1.05 eq) in THF (100 mL) was added dropwise at -70C, the reaction mixture was stirred at -70C for 2 hr. The reaction mixture was quenched by water (300 mL) and extracted with EtOAc (200 mLx2). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash column chromatography on silicagel (Petroleum ether/EtOAc 10/1 to 5/1). Intermediate 2a (24.00 g, 86.00 mmol, 79.57% yield) was obtained as a light yellow solid. 1H NMR (DMSO-d6; 400MHz) delta 7.31-7.29 (m, 1H), 6.90-6.89 (m, 2H), 4.66 (s, 1H), 3.87 (s, 4H), 2.49 (s, 3H), 2.21 (s, 3H), 2.00-1.94 (m, 4H), 1.79-1.76 (m, 2H), 1.53-1.51 (m, 2H).

According to the analysis of related databases, 583-70-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pragma Therapeutics; DUVEY, Guillaume; CELANIRE, Sylvain; (118 pag.)EP3459939; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 583-70-0, A common heterocyclic compound, 583-70-0, name is 2,4-Dimethylbromobenzene, molecular formula is C8H9Br, 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.

A dried round-bottom flask containing stir bar was charged with magnesium (530 mg, 21.70 mmol), small piece of iodine and dry THF (73 mL) was added under argon. Solution of 1-bromo-2,4-dimethylbenzene (3.65 g, 19.72 mmol) diluted in dry THF (3 mL) was added dropwise to the suspension and the solution was stirred at 50C for 60 mm. After the formation of Grignard reagent,_the_reaction_mixture_was_cooled_to_0C,_and_then_N-[(3-chlorophenyl)methylidene]-2-methylpropane-2-sulfinamide Ex.83a (3.37 g, 13.81 mmol) in dryTHF (3 mL)was added dropwise. The resulting mixture was stirred at rt. After the completion of the reaction, the reaction mixture was quenched with sat. NH4CI and the solution was extracted with EtOAc. The combined organic layers were washed with brine. After phases separation, the organic layer was dried over MgSO4, filtered and the solution was concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with a gradient of Hexanes/EtOAc from [90:10] to [60:40] to afford N-[(3-chlorophenyl)(2,4-dimethylphenyl)methyl]-2- methylpropane-2-sulfinamide Ex.83b (2.30 g, 48%) as yellow oil. 1 H NMR (400 MHz, DMSO-d6, din ppm): 1.11 (s, 9H), 2.22 (s, 3H), 2.26 (s, 3H), 5.67 (d, 1H, J=6.3Hz), 6.03 (d, 1H, J=6.3Hz), 6.98 (s, 1H), 7.04 (d, 1H, J=8.OHz), 7.19-7.27 (m, 1H), 7.26-7.40 (m, 4H).

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; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; (284 pag.)WO2018/138362; (2018); 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. 583-70-0, name is 2,4-Dimethylbromobenzene, A new synthetic method of this compound is introduced below., Formula: C8H9Br

General procedure: A flask furnishedwith a dropping funnel was charged with the aryl/alkylbromide in Et2O. n-BuLi(1.6 M in hexane) diluted with Et2O was added dropwise at -78C. After addition, thereaction was kept at -78C for 10 min and was then allowed to warm to room temperatureand stirred for 30 min. The solution was transferred via cannula to SiCl4 dissolved in Et2Oat 0C. The reaction was stirred for 2 h and was allowed to warm to room temperature. Thesolvent was removed under reduced pressure and the residue dissolved in boiling toluene.Insoluble salts were removed via filtration through cellite and washed with hot toluene. Thesolvent from the resulting clear solution was removed under reduced pressure, followed bypurification via distillation or recrystallization.

The synthetic route of 583-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Binder, Judith; Fischer, Roland C.; Flock, Michaela; Torvisco, Ana; Uhlig, Frank; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 190; 11; (2015); p. 1980 – 1994;,
Bromide – Wikipedia,
bromide – Wiktionary

583-70-0, name is 2,4-Dimethylbromobenzene, belongs to bromides-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. Formula: C8H9Br

Under a nitrogen atmosphere, cuprous iodide (3.0 mol%, 0.7 mg), sodium iodide (1.0 equiv., 18.7 mg) and magnets were added to a previously baked 10 mL glass pressure tube. Dioxane (0.2 mL), 2,4-dimethylbromobenzene (0.125 mmol, 1.0 equiv., 23.2 mg) and N,N’-dimethylethylenediamine (10.0 mol%, 1.1 mg) were then added. ). After the addition was completed, the glass pressure tube was placed in a metal module that had been preheated to 100 deg C and stirred for 10 hours. After cooling to room temperature, copper powder (20 mol%, 1.6 mg), aluminum chloride (3 mol%, 0.5 mg), N-methylpyrrolidone (0.5 mL) and polymethylhydrogensiloxane (3.0 equiv) were added under a nitrogen atmosphere. ., 83.4mg). The tube was purged of air and charged with carbon dioxide (5.0 equiv., 15 mL) and ammonia gas (5.0 equiv., 15 mL). After the addition was completed, the reactor was placed in a metal module preheated to 160 deg C and stirred for 10 hours. After the reaction was completed, the reaction system was cooled to room temperature and pressure was slowly released. Using dodecane as an internal standard, the yield of the gas chromatogram was determined to be 78%.

The synthetic route of 583-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Lanzhou Chemical Physics Institute Suzhou Institute; Li Yuehui; Wang Hua; Dong Yanan; Ke Lisitian·shanduofu; (20 pag.)CN108017557; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary