Month: March 2021

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. 1422-53-3, name is 2-Bromo-4-fluorotoluene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2-Bromo-4-fluorotoluene

To a solution of 2-bromo-4-fluorotoluene (16.0 g) in anhydrous tetrahydrofuran was added dropwise at -78 C. a solution of 1.6M butyllithium in hexane (55.5 ml), and the mixture was stirred at the same temperature for 30 minutes. To the mixture was added dropwise a solution of dimethylformamide (6.8 g) in tetrahydrofuran (20 ml), and the mixture was allowed to stand to warm up to 0 C. To the reaction solution was added ice-water, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give oil of 5-fluoro-2-methylbenzaldehyde (11.5 g). To a mixture of acetone (80 ml), sodium hydroxide (3.7 g) and water (100 ml) was added dropwise at room temperature a solution of 5-fluoro-2-methylbenzaldehyde (11.5 g) in acetone (30 ml), and the mixture was stirred at the same temperature for 1 hour. Under reduced pressure, acetone was evaporated, and the residue was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and concentrated under reduced pressure to give 4-(5-fluoro-2-methylphenyl)-3-buten-2-one (13.4 g). To a solution of 20% sodium ethoxide in ethanol (5.9 g) was added at room temperature diethyl malonate (14.0 g), and then added little by little 4-(5-fluoro-2-methylphenyl)-3-buten-2-one (13.4 g), and the mixture was stirred at room temperature for 30 minutes and then for 2 hours while heating, and cooled. The solvent was evaporated, and to the residue was added water. The aqueous layer was washed with ethyl acetate and concentrated. To the residue was added 2M sodium hydroxide (46 ml), and the mixture was refluxed for 2 hours and cooled. To the mixture was added 2.5M sulfuric acid (46 ml) for 10 minutes, and the mixture was refluxed for 30 minutes and cooled. Precipitated crystals were filtered and washed with water and isopropylether to give 5-(5-fluoro-2-methylphenyl)cyclohexane-1,3-dione (8.6 g) as colorless crystals. mp 175-176 C. 1H-NMR(CDCl3) delta: 2.30 (3H, s), 2.27-2.56 (4H, m), 2.5-4.3 (1H, br), 3.44-3.63 (1H, m), 5.55 (1H, s), 6.77-7.01 (2H, m), 7.09-7.17 (1H, m).

The synthetic route of 1422-53-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6350749; (2002); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 4263-52-9, name is Sodium 2-bromoethanesulphonate, 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 Sodium 2-bromoethanesulphonate

b) Compound lb; [0169] A mixture of compound la, (0.1 g, 0.45 mmole), sodium 2- bromoethanesulfonate (0.19 g, 2 equivalents) and 2,6-di-tert-butylpyridine (99 muL, 0.45 mmole) in [BMIM]BF4] (1 mL, Aldrich) was heated in an oil bath at 150C with vigorous stirring for 16 hours. The reaction was then cooled to room temperature and a small portion of the reaction mixture was withdrawn, diluted with methanol/water and analyzed by analytical HPLC using a Phenomenex, Ci8,4.6 x 250 mm column and a 30 minute gradient of 10? 70% MeCN/water (with 0.05% TFA) at a flow rate of 1.0 mL/minute and UV detection at 260nm and 220 nm. Product was observed eluting at Rt = 13.3 minutes (-40% conversion). The reaction mixture was prepared by diluting it with water (15 mL) and washing this solution with ethyl acetate (2 x 25 mL). The aqueous solution was then treated with 3 to 4 drops of ammonia and further extracted with ethyl acetate (2 x 25 mL). The aqueous solution was then concentrated to about 7 mL by rotary evaporation. The product was then purified by preparative HPLC using an YMC, Ci8, 30 x 250 mm column and the same gradient as described above at a flow rate of 20 mL/minute. HPLC fractions containing product were combined and concentrated under reduced pressure. Yield = 30 mg (20%, white solid); MALDI-TOF MS 330.6 observed.

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

Reference:
Patent; SIEMENS HEALTHCARE DIAGNOSTICS INC.; NATRAJAN, Anand; SHARPE, David; WEN, David; JIANG, Qingping; WO2011/146595; (2011); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 129316-09-2,Some common heterocyclic compound, 129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene, molecular formula is C10H12Br2, 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.

Step 1 : tert-Butyl 3-bromo-5-(tert-butvnbenzoate (P11a)n-BuLi (7.2 mL, 18.0 mmol, 2.5M in THF) was added to a flask under N2 containing toluene (9 mL) at -10C. >BuMgCI (4.5 mL, 9.0 mmol, 2M in THF) was then added at such a rate to keep the temperature below -5C. The resulting milky slurry was aged at -10C for 30 min, then 1 ,3- dibromo-5-(terf-butyl)benzene (6.2 g, 21.2 mmol) dissolved in toluene (20 mL) was added. The rate of addition was such that the temperature did not increase above -5C. After addition was complete, the mixture was kept at -10C until the metal-halogen reaction was complete. A solution of di-tert-butyl dicarbonate (5.89 g, 27 mmol) in toluene (7.5 mL) was then charged such at a rate to keep the temperature below -5C. After the addition was complete, the mixture was kept at -10C until the aryl-Mg intermediate was completely consumed. The mixture was quenched by the addition of 10% aq. citric acid (40 mL). The phases were separated and the organic layer was washed with another 10% aq. citric acid (40 mL). The organic extracts were dried over MgS04 and concentrated. Compound P11a (4.0 g, 60%) was obtained as a brown oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dibromo-5-(tert-butyl)benzene, its application will become more common.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas; WO2012/139775; (2012); 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. 22364-29-0, name is 2-Bromo-4,5-dimethylaniline, A new synthetic method of this compound is introduced below., COA of Formula: C8H10BrN

To a suspension of aniline ii (20.0 g, 100 mmol) in H2O (50 mL)was added 12 M HCl (100 mL) and the reaction mixture was cooled to 0 C, to which was gradually added NaNO2 (8.99 g, 130 mmol) in H2O (30 mL) followed by CuCl (12.1 g, 122 mmol) dissolved in 12 M HCl (30 mL) at same temperature. After warmed up to room temperature, the reaction was stirred for further 20 min. The products were extracted with Et2O (X3), and the combined organic extracts were washed with 25% NH3 aq. and brine, dried (Na2SO4), and concentrated in vacuo. Purification of the crude products by recrystallization from MeOH gave 1-bromo-2-chloro-4,5-dimethylbenzene (iii) (15.2 g, 69.2%) as colorless prisms.

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:
Article; Eda, Shohei; Hamura, Toshiyuki; Molecules; vol. 20; 10; (2015); p. 19449 – 19462;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 33070-32-5, These common heterocyclic compound, 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, 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.

Preparation 67 2-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane To a solution of 5-bromo-2,2-difluorobenzo[d][1,3]dioxole (1.5 g, 6.3 mmol) in N,N-dimethylformamide (12.7 mL) was added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (1.6 g, 6.3 mmol), potassium acetate (1.9 g, 19.0 mmol), and (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.3 g, 0.32 mmol). The reaction mixture was heated at 80 C. for 18 h, then the reaction mixture was diluted with Et2O and washed with water. The organic layers were separated, dried with Na2SO4, filtered, concentrated in vacuo, and purified by silica gel chromatography eluting with 0-100% acetone in hexanes to yield a brown oil (0.9 g, 50%): 1H NMR (400 MHz, DMSO-d6) delta 7.55 (d, J=8.0 Hz, 1H), 7.53 (s, 1H), 7.43 (d, J=8.0 Hz, 1H), 1.30 (s, 12H); 19F NMR (376 MHz, DMSO-d6) delta -49.26 (s); EIMS m/z 284.

The synthetic route of 33070-32-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; Eckelbarger, Joseph D.; Epp, Jeffrey B.; Fischer, Lindsey G.; Lowe, Christian T.; Petkus, Jeff; Roth, Joshua; Satchivi, Norbert M.; Schmitzer, Paul R.; Siddall, Thomas L.; US2014/274701; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 393-36-2, These common heterocyclic compound, 393-36-2, name is 4-Bromo-3-(trifluoromethyl)aniline, 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.

4-Bromo-3-(trifluoromethyl)aniline was converted into 4-bromo-3-(trifluoromethyl)phenyl isocyanate according to Method B1. According to Method C1a, 4-bromo-3-(trifluoromethyl)phenyl isocyanate was reacted with 4-(2-(N-methylcarbamoyl)-4-pyridyloxy)-2-chloroaniline to afford the urea. Entry 87: According to Method A2, Step 4, 4-amino-2-chlorophenol was reacted with 4-chloro-N-methyl-2-pyridinecarboxamide, which had been synthesised according to Method A2, Step 3b, to give 4-(2-(N-methylcarbamoyl)-4-pyridyloxy)-3-chloroaniline.

The synthetic route of 393-36-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CORPORATION; US2003/144278; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 38573-88-5, 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 38573-88-5 as follows.

Isopropylmagnesiumchloride-LiCl complex (1,30 M in THF, 155.0 mL, 0.0715 mol) under nitrogen was cooled to 0-5 ¡ãC, and 2,3-difluorobromobenzene (13.8 g, 0.0715 mol, 1.50 equiv.) was added while T < 10 ¡ãC. After 1 h at 0-5 ¡ãC, a solution of 1 -morpholino-2-( 1 -(trityloxy)but-3-en-2-yloxy)ethanone 14 (21.8 g, 0.048 mol, 1.0 equiv.) in THF (2.0 vols) was added while T <10 ¡ãC. The reaction mixture was stirred for 2.5 hours and monitored for consumption of 1-morpholino-2-(l-(trityloxy)but-3-en-2-yloxy)ethanone (target >97percent). The reaction mixture was quenched by charging into cold sat. aq. NH4CI (110 mL) and water (33 mL) while T < 20 ¡ãC. 2-Methoxy-2-methylpropane (218 mL) was added and the layers were separated. The organics were washed with sat. aq. NH4CI (65 mL) and 18percent aq. NaCl (44 mL.). The organics were concentrated under vacuum T < 25 ¡ãC to a light yellow oil of ketone 15 (21.6 g). According to the analysis of related databases, 38573-88-5, the application of this compound in the production field has become more and more popular. Reference:
Patent; ???????????????????????????; ? Buranko; Kimu ?; Chan ?; ?; Yoshizawa Kazuhiro; (94 pag.)JP2016/121177; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 17247-58-4, 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. 17247-58-4, name is (Bromomethyl)cyclobutane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(5-Bromo-7-methyl-l-oxo-l,3-dihydiO-isoindol-2-yl)-carbamic acid tert-butyl ester (0.05g, 0.146 mmol), bromomethyl cyclobutane (0.033 mL, 0.293 mmol) and cesium carbonate (0.12 g, 0.366 mmol) were stirred in acetonitrile (3 mL) at 70 0C for 3 hours. The reaction mixture was partitioned with dichloromethane and water and the aqueous phase was further extracted with dichloromethane. The organic extracts were washed with water, brine, dried over sodium sulfate, filtered and concentrated. The product residue was purified by eluting through a solid phase extraction tube eluting with ethyl acetate:hexanes (2:98 to 5:95) to yield the product as a colorless oil (0.048 g, 80%). 1H NMR (300 MHz, CDCI3): 5 7.39 (d, 2H), 6.71 (br s, IH), 4.46 (s, 2H), 2.68 (s, 3H), 1.42 (s, 9H).

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, (Bromomethyl)cyclobutane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2008/130853; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1647-26-3, These common heterocyclic compound, 1647-26-3, name is 1-Bromo-2-cyclohexylethane, 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 stirred solution of tert-butyl {6-[({[( 1 -methyl- 1 H-tetrazol-5- yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate (0.2 g, 0.488 mmol, 1 eq.) in 3 ml of dry DMF was treated with NaH (60% dispn in mineral oil, 0.020 g, 0.513 mmol, 1.05 eq.) added in one portion. After 20 mins (2-bromoethyl)cyclohexane (0.098 g, 0.513 mmol, 1.05 eq.) was added and the reaction was stirred for 1 hr. Water was added followed by EtOAc. The aqueous layer was separated and extracted with EtOAc. Then the organics were combined, dried over MgSO4 and evaporated to give tert-butyl (2-cyclohexylethyl){6-[({[(1-methyl-1 H-tetrazol-5- yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate (0.27 g, 85 %) as a viscous oil HPLC/MS : m/z = 520 (M+H) ; logP(HCooH) = 6.56

The synthetic route of 1647-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE SA; WO2009/115557; (2009); A2;,
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. 201138-91-2, name is 4,6-Dibromodibenzo[b,d]furan, A new synthetic method of this compound is introduced below., name: 4,6-Dibromodibenzo[b,d]furan

26.9 g Intermediate (22) and 37.8 g 4,6-dibromo dibenzofuran were added into a dry 2 L three-neck flask, followed by adding 800 mL dry and degassed toluene to dissolve. Then, 33.4 g sodium tert-butoxide (3.0 eq.), 0.52 g catalyst palladium diacetate (2% mol) and 2.9 g 1,1?-binaphthyl-2,2?-bis(diphenylphosphino) (BINAP, 4% mol) ligand were added. The reaction mixture was heated up to 110 C. and reacted overnight. After the reaction finished and the reaction mixture was cooled down to room temperature. The residual was absorbed by the added activated carbon, filtered by suction filtration and removed with solvent by rotary evaporation, followed by recrystallization with a mixture of toluene and ethanol, to produce 47.6 g Intermediate (23) at a yield of 90%.

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; NANJING TOPTO MATERIALS CO.,LTD.; KIM, JIN WOO; QIAN, CHAO; GAO, PENGHUI; WANG, XIAOWEI; (157 pag.)US2018/105534; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary