Month: May 2021

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. 1003-98-1, name is 2-Bromo-4-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., category: bromides-buliding-blocks

Step 1: 2-(2-Bromo-4-fluorophenyl)hydrazinium chlorideTo a suspension of 2-bromo-4-fluoroaniline in concentrated HCl (1.5M) at -10 0C was slowly added a 10.0M aqueous solution OfNaNO2 (1.1 eq). The mixture was stirred at O 0C for 2.5 hrs. A cold (-30 C) solution Of SnCl2 (3.8M) in concentrated HCl was then slowly added while maintaining the internal temperature below 10 0C. The resulting mixture was stirred mechanically for 20 mm at 10 C, then at room temperature for 1 hr. The thick slurry was filtered and the solid was air dried overnight. The solid was resuspended in cold HCl and filtered again. The dried material was suspended in Et2O, stirred for 10 min, filtered and air dried overnight to give the title compound as a beige solid

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 1003-98-1.

Reference:
Patent; MERCK & CO., INC.; WO2006/89309; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1435-51-4, A common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, molecular formula is C6H3Br2F, 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.

Sodium hydride (9.9 g, 0.414 mol, 95% dry) was added in portions to a stirred solution of benzyl alcohol (41.0 g, 0.394 mol) in THF (1.0 L) at room temperature under a nitrogen atmosphere and stirred for 1 h. To this solution was added dropwise 1,3-dibromo-5-fluorobenzene (100.0 g, 0.394 mol). After stirring overnight, the mixture was partitioned with H2O (600 mL) and EtOAc (4*600 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. Flash chromatography on silica gel eluding with hexanes afforded the sub-title compound (101.3 g, 75%) as a yellow oil. 1H NMR (300 MHz, CDCl3) delta7.30-7.48 (m, 5H), 7.18 (s, 1H), 7.06 (s, 2H), 4.99 (s, 2H).

The synthetic route of 1435-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Inghardt, Tord; Johansson, Anders; Svensson, Arne; US2004/19033; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 69321-60-4, name is 2,6-Dibromotoluene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H6Br2

n-BuLi in hexanes (2.5 M; 8.1 mL, 20 mmol) was added dropwise to a solution of 1,3-dibromo-2-methylbenzene (4.8 g, 19 mmol) in THF (50 mL) at -78 C. at such a rate as to keep the internal reaction temperature below -60 C. After stirring for 30 minutes, tert-butyl (R)-4-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (5.01 g, 21.1 mmol) was added in portions, and the reaction was stirred for a further 30 minutes before being allowed to warm to 0 C. over 2 hours. Aqueous citric acid (1N; 40 mL) was added at 0 C., and the mixture was stirred for 15 min before it was extracted with EtOAc (2*100 mL). The combined organic layers were concentrated under reduced pressure. The residue was stirred in HCl in dioxane (4N; 30 mL) at room temperature for 1 hour and then concentrated. The resulting residue was dissolved in water (100 mL) and extracted with diethyl ether (2*60 mL). The aqueous layer was then basified by addition of Na2CO3 and extracted with DCM (3*100 mL). The combined DCM extracts were dried over Na2SO4, filtered and concentrated to dryness. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Product fractions were concentrated to dryness to afford (R)-1-(3-bromo-2-methylphenyl)propan-2-amine (2.6 g, 60%) as a brown oil. 1H NMR (500 MHz, DMSO-d6, 27 C.) 1.1 (3H, d) 2.34 (3H, s) 2.64 (1H, dd) 2.77 (1H, dd) 3.08 (1H, ddd) 7.05 (1H, t) 7.15 (1H, d) 7.45 (1H, d). NH2 was not observed. m/z: ES+ [M+H]+ 228.

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 69321-60-4.

Reference:
Patent; AstraZeneca AB; YANG, Bin; VARNES, Jeffrey Gilbert; SCOTT, James Stewart; MOSS, Thomas Andrew; O’DONOVAN, Daniel Hillebrand; NISSINK, Johannes Wilhelmus Maria; HUGHES, Samantha Jayne; BARLAAM, Bernard Christophe; (83 pag.)US2017/305909; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 2924-09-6, name is 5-Bromo-2-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., category: bromides-buliding-blocks

A mixture of 5-bromo-2-fluoroaniline (10 g, 52.6 mmol), 3- (trifluoromethyl)benzene-1-sulfonyl chloride (12.9 g, 52.6 mmol) and pyridine (30 mL) was stirred overnight at 60oC. The pH value of the solution was adjusted to 3-4 with 1M aqueous hydrogen chloride. The mixture was extracted three times with dichloromethane. The combined organic layers combined were dried (Na2SO4) and concentrated. The residue was purified via MPLC eluting with 10% ethyl acetate in petroleum ether to afford N-(5-bromo-2- fluorophenyl)-3-(trifluoromethyl)benzenesulfonamide (19.3 g, 92%) as a light yellow solid.

According to the analysis of related databases, 2924-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LYCERA CORPORATION; AICHER, Thomas, Daniel; TAYLOR, Clarke, B.; VANHUIS, Chad, A.; (410 pag.)WO2016/201225; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 10016-52-1, 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. 10016-52-1, name is 2,8-Dibromodibenzo[b,d]furan, This compound has unique chemical properties. The synthetic route is as follows.

Under a stream of nitrogen, 0.46 g (1.4 mmol) of 2,8-dibromodibenzofuran (manufactured by Sigma-Aldrich Co. LLC.) and 0.90 g (2.8 mmol) of Exemplified Compound 18-1 were added to 15 ml of DMSO and 0.89 g (4.2 mmol) of potassium phosphate and stirred for 10 minutes. To the resultant, 53 mg (0.28 mmol) of CuI and 6-methyl picolinic acid (0.56 mmol) were added and heated at 125 C. for 7 hours. Under cooling with water, 5 ml of water was added thereto and stirred for 1 hour. The precipitated crude product was filtered, further subjected to the column purification, and then recrystallized with o-dichlorobenzene/acetonitrile so as to obtain 0.80 g (yield of 71%) of Exemplified Compound 18.

The chemical industry reduces the impact on the environment during synthesis 2,8-Dibromodibenzo[b,d]furan. I believe this compound will play a more active role in future production and life.

Reference:
Patent; KONICA MINOLTA, INC.; Okubo, Yasushi; Itoh, Hiroaki; Wachi, Ayako; Ishidai, Hiroshi; (69 pag.)US9941422; (2018); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1073-39-8, A common heterocyclic compound, 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, molecular formula is C8H7Br, 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 magnetic stir bar and 3.10 g of magnesium strip were added to the reactor.The vacuum was purged with nitrogen three times (to ensure the removal of oxygen in the system), and 6 mL of tetrahydrofuran and 0.010 g of iodine activated magnesium strip were added to the reactor under nitrogen protection.20 g of 4-bromobenzocyclobutene was diluted in 36 mL of tetrahydrofuran to obtain a mixed solution.A few drops of the mixed solution was added dropwise at room temperature, and the reaction was initiated by contact with magnesium strips and iodine. After the reaction of tetrahydrofuran was slightly refluxed, the mixed solution was slowly added dropwise, and the addition was completed in 2 hours.After the addition was completed, the system was transferred to a 70 C oil bath for 2 h. The temperature was lowered to room temperature under a nitrogen atmosphere, and 14 g of dimethylvinylchlorosilane was diluted in 30 mL of tetrahydrofuran to obtain a mixed solution.The mixture was slowly added dropwise to the human system, and the addition was completed in 2 hours. After the completion of the dropwise addition, the system was transferred to a 70 C oil bath, and the reaction was continued for 2.5 h to obtain an off-white slurry.Separation and purification: After the reaction is completed, the obtained off-white slurry is cooled to room temperature.The excess Grignard reagent was quenched by the addition of 3 mol/L of dilute hydrochloric acid (the amount of dilute hydrochloric acid added was allowed to react the remaining magnesium strips in the reaction).It was extracted with 25 mL of n-hexane, extracted three times, and the organic phases were combined. After washing with dilute hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution,It was dried over anhydrous sodium sulfate for 5 h. Filtration and concentration of the filtrate on a rotary evaporator afforded a pale yellow liquid.The liquid was subjected to distillation under reduced pressure and a fraction having a temperature of 80 C was collected to obtain a colorless transparent liquid, which was a 4-dimethylvinylsilylbenzocyclobutene (4-DMVSBCB).

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; Southwest University of Science and Technology; Yang Junxiao; Wei Xuelian; Yin Qiang; Hu Huan; Li Xian; Fan Li; Ma Jiajun; (14 pag.)CN108503664; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 53078-85-6, 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 53078-85-6 as follows.

General procedure: A dried tube, equipped with a magnetic stirred and a septum, 2-bromoaniline (0.17 g,1.0mmol) was dissolved in DMSO (3mL), KOt-Bu (0.34 g, 3mmol) was added. The mixturewas stirred for 5 min, and then dithiocarbamate (0.296 g, 1.5mmol) and copper oxide(6.4mg, 8 mmol%) were added. The reaction mixture was heated at 100C and checkedby TLC until the starting material was finished. The reaction mixture was cooled downto room temperature, and then quenched with sat. NH4Cl solution (5mL) and extractedwith ethyl acetate, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by flash column chromatography to afford the desired product(144mg, 81%).

According to the analysis of related databases, 53078-85-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Xu, Wan; Zeng, Meng-Tian; Liu, Min; Liu, Xing; Chang, Cai-Zhu; Zhu, Hui; Dong, Zhi-Bing; Journal of Sulfur Chemistry; vol. 38; 6; (2017); p. 644 – 654;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 327-52-6, 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 327-52-6 as follows.

In a 5L dry reaction flask, dried 1.5kg of tetrahydrofuran and 40g of 2-chloropropane were added, and the temperature was raised to microfluidic (60C), then, 5 ml of isopropylmagnesium chloride was added dropwise to initiate the reaction, after the reaction is stable, the remaining 2-chloropropane 350g was slowly added drop wise, and the temperature was controlled to maintain micro reflux (68-72), and reflux was added dropwise for 2 hours (until complete reaction of magnesium chips, if any magnesium chips were left, 2-chloropropane was added. ), cooled to room temperature after the reaction, in a 30L reactor, 1.3kg of dried tetrahydrofuran, 1.3kg of toluene and 682g of trifluorobromobenzene were added, and the nitrogen protection of the reaction solution was lowered to a temperature of -25C, the temperature is controlled below -20C, and 2kg of isopropylmagnesium chloride was added dropwise, the incubation reaction was completed for one hour after dropping, monitored by HPLC, cuprous chloride 24g was added, then , heated and stirred for 30 minutes, a solution of 0.5 kg of a solution of compound 3 (512 g) in toluene was added dropwise, the reaction was carried out from minus 5C to minus 2C for 16 hours, monitored by HPLC, kg of saturated aqueous ammonium chloride solution (quenching effect) was added dropwise below 5C, the temperature was controlled below 10C, and about 1.5 kg of 3N hydrochloric acid was added dropwise to adjust the pH to approx 4. The aqueous phase was extracted once with 0.5L of toluene, the organic phases were combined and washed once with diluted aqueous ammonia (concentrated aqueous ammonia 100g watered with 0.5kg) and washed twice with 0.5kg semi-saturated brine, the aqueous phase was combined and extracted once with 0.5kg toluene, and toluene was distilled under reduced pressure at 45-55C, when the reaction liquid becomes a paste, 2 kg of water was added, concentration was continued until the distilled out solvent was water. 1kg of methanol was added, beaten overnight, and filtered, filter cake was washed twice with water, and the product was dried by blowing at 65C to obtain Compound 4 (720g) as a pale yellow powder in a yield of 85%.

According to the analysis of related databases, 327-52-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Heding (Nanjing) Pharmaceutical Co., Ltd.; Li Wensen; (18 pag.)CN107540575; (2018); 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 2255-80-3 as follows. Product Details of 2255-80-3

4-Bromo-7-methylbenzo[c][l,2,5]thiadiazole (0.5 g, 2.2 mmol) was suspended in methanol (7 ml) and warmed to 45 0C (internal temperature). The suspension was then treated with magnesium turnings (0.42 g, 17.6 mmol) and stirred for 30 mins. The reaction was then cooled and the methanol removed in vacuo. The residue was then mixed with aq. NH4Cl and extracted with EtOAc (3 x 30 ml). The organic layers were dried over MgSO4, filtered, concentrated and dried in vacuo to afford 3-bromo- 6-methylbenzene-l,2-diamine (0.39 g, 94%); deltaH(400 MHz, CDCl3) 6.88 (IH, d, J 8, Ar-H), 6.47 (1H, d, J 8, Ar-H), 3.60 (4H, bs, Ar-NH2), 2.16 (3H, s, ArCH3); m/z (EI) 202 ([81Br]M+, 95%), 200 ([79Br]M+, 100%), 120 (M+ -Br, 75%); the resultant solid was used directly in the next stage.46.

According to the analysis of related databases, 2255-80-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF DURHAM; WO2009/34396; (2009); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 418762-26-2, These common heterocyclic compound, 418762-26-2, name is 4-Bromo-2-fluoro-5-methylaniline, 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.

EXAMPLE 73 7-(2,6-dichlorobenzyl)-5-{ [2-fluoro-5-methyl-4-(piperazin-l -yl)phenyl]amino}pyrido[3,4- d]pyridazin-4(3H)-one EXAMPLE 73A /V,jV-dibenzy l-4-bromo-2-fluoro-5-methylbenzenamineA suspension of 4-bromo-2-fluoro-5-methylbenzenamine (1 g, 4.9 mmol), benzylbromide (2.5 g, 14.7 mmol) and potassium carbonate (2 g, 14.7 mmol) in acetonitrile (80 mL) was heated in a sealed tube at 100C for 16 hours. After concentration, the residue was diluted with ethyl acetate (80 mL) and washed with water (20 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and purified by flash chromatography on silica gel (200-300 mesh) eluting with 50/1 petroleum ether/ethyl acetate to give the title compound. MS : 384 (M+H+).

Statistics shows that 4-Bromo-2-fluoro-5-methylaniline is playing an increasingly important role. we look forward to future research findings about 418762-26-2.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97682; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary