Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 17247-58-4, name is (Bromomethyl)cyclobutane, 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 17247-58-4, Formula: C5H9Br

To a solution of deprotected phenol derivative 20 (0.3 g, 0.571 mmol) in dimethylformamide (10 mL) was added sodium hydride (50 mg, 2.083 mmol) and K2CO3 (0.8 g, 5.79 mmol) at 0 C, stirred for 15 min, followed by addition of (bromomethyl)cyclobutane (90 mg, 0.602 mmol). After completion of addition, ice-bath was removed and the reaction mixture was stirred at rt for 4 h. Upon completion of the reaction, mixture was poured into ice-water (250 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic layer was washed with saturated aq. NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo to obtain the crude product. The crude product was purified using column chromatography (n-hexane/EtOAc 60:40) to obtain 6-O-(cyclobutyl)methyl derivative 39 (0.27 g, 75%) TLC: Rf = 0.64 (n-hexane/EtOAc 50:50). m.p. = 145-147 C. 1H-NMR (400 MHz, CDCl3) delta 0.33 (d, J = 4.4 Hz, 4H), 0.56 (d, J = 7.8 Hz, 2H), 1.05 (t, J = 7.1 Hz, 3H), 1.20 (t, J = 7.4 Hz, 1H), 1.27 (t, J = 7.5 Hz, 3H), 2.65 (q, J = 7.5 Hz, 2H), 3.89 (d, J = 6.4 Hz, 2H), 3.99 (s, 2H), 4.24 (q, J = 7.1 Hz, 2H), 5.19 (s, 2H), 5.85 (s, 2H), 6.21 (s, 1H), 6.74 (s, 1H), 7.08 (d, J = 9.4 Hz, 1H), 7.11 (dd, J = 9.3 Hz, 1H), 7.31 (t, J = 7.7 Hz, 1H), 7.60 (d, J = 7.6 Hz, 1H), 7.82 (s, 1H), 7.84 (d, J = 8.9 Hz, 1H), 7.99 (s, 1H).

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:
Article; Khadtare, Nikhil; Stephani, Ralph; Korlipara, Vijaya; Bioorganic and Medicinal Chemistry Letters; vol. 27; 11; (2017); p. 2281 – 2285;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 2606-51-1, 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. 2606-51-1, name is 5-(Bromomethyl)benzo[d][1,3]dioxole, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of 6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1 ,5-a]pyrazin-8(7/-/)-one (100 mg, 429 mol) in dry DMF (2 mL) was added Cs2C03 (279 mg, 858 Mmol) and 5- (bromomethyl)benzo[d][1 ,3]dioxole (138 mg, 643 imol). The mixture was bubbled with 2 for 2 min and heated at 60C for 16 hours. The mixture was concentrated. DCM (30 mL) was added to the residue. It was filtered and the filter cake was washed with DCM (20 mL). The filtrate was concentrated and purified by flash chromatography on silica gel (10%~100% ethyl acetate in petroleum ether) to give 7-(benzo[d][1 ,3]dioxol-5-ylmethyl)-6-methyl-3- (tetrahydro-2H-pyran-4-yl)imidazo[1 ,5-a]pyrazin-8(7/-/)-one (81.74 mg, 52% yield). (1018) 1H NMR (CDCIa 400 MHz): delta 7.92 (s, 1 H), 6.76 – 6.69 (m, 4H), 5.95 – 5.93 (m, 2H), 5.13 (s, 2H), 4.14 – 4.11 (m, 2H), 3.61 – 3.55 (m, 2H), 3.10 – 3.05 (m, 1 H), 2.21 (s, 3H), 2.20 – 2.10 (m, 2H), 1.90 – 1.86 (m, 2H). (1019) LC-MS: fR = 2.245 min (method 3), m/z = 368.2 [M + H]+.

The chemical industry reduces the impact on the environment during synthesis 5-(Bromomethyl)benzo[d][1,3]dioxole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (159 pag.)WO2018/78042; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 626-88-0, The chemical industry reduces the impact on the environment during synthesis 626-88-0, name is 1-Bromo-4-methylpentane, I believe this compound will play a more active role in future production and life.

Step 1. Preparaion of 1-Chloro-8-methyl-4-nonanone To the Grignard reagent prepared from a mixture of 1-bromo-4-methylpentane (200.00 g.; 1.21 mole) and magnesium (29.43 g.; 1.21 mole) in ether (800 ml.) is added, dropwise during one hour, 4-chlorobutyronitrile (125.30 g.; 1.21 mole). Stirring is continued for an additional one hour. The reaction mixture is poured into a mixture of finely crushed ice (800 g.) and concentrated hydrochloric acid (600 ml.). The ether layer is separated quickly and discarded. The aqueous layer is heated on a steam bath for one hour to hydrolyze the intermediate imine and cause the separation of the ketone as an oil. After cooling, the oil is extracted with ether and the combined extracts are washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent is removed under vacuum and the residual oil is distilled to give 23.3 g. (10%) of colorless oil, b.p. 121-122/15 mm.; pmr (CDCl3)delta 0.89 (6H,d), 3.57 (2H,t CH2 Cl). Anal. Calcd. for C10 H19 ClO: C, 62.98; H, 10.04. Found: C, 62.86; H, 10.20.

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

Reference:
Patent; Merck & Co., Inc.; US4055597; (1977); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 43204-63-3, name is Bis(2-Bromoethyl)amine hydrobromide, 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 43204-63-3, Safety of Bis(2-Bromoethyl)amine hydrobromide

a Synthesis of 2-bromo-N-(2-bromoethyl)-N-carbobenzoxyethanamine (1c): Benzyl chloroformate (1.97 ml, 13.8 mmol) and 1M sodium hydroxide solution is added with vigorous stirring to an ice-cold solution of bis(2-bromoethyl)amine hydrobromide (4.5 g, 14.4 mmol) in water (25 ml) until the pH is just basic (about 24 ml). The mixture is acidified with 1M hydrochloric acid (2 ml) and extracted with ether (3*40 ml). The organic phase is washed with sodium hydrogen carbonate solution and water, dried over magnesium sulfate and concentrated, and the residue is chromatographed (hexane/ethyl acetate 5:1?4:1). Compound 1 c (4.1 g, 81%) is obtained. 1 H-NMR (300 MHz, CDCl3): delta=3.43, 3.53 ?2 m, 4H, N(CH2 –CH2 Br)2!, 3.73 ?m, 4H, N(CH2 –CH2 Br)2!, 5.17 (s, 2H, CH2 Ph), 7.36 (m, 5H, Ph).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Hoechst Aktiengesellschaft; US5739300; (1998); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 348-57-2, 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. 348-57-2, name is 1-Bromo-2,4-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

A total of 1.6 g of 1-bromo-2,4-difluorobenzene was suspended in 8.29 ml of sulfuric acid, and 1.62 g of N-bromosuccinimide was added under ice-cooling. After stirring at room temperature for 17 hours, the reaction mixture was poured onto ice-water and extracted with ethyl acetate. The resulting organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine, dried over magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (hexane), to give 2.18 g of the title compound as a pale yellow oil.1H-NMR ( 400MHz, CDCl3 ) d 6.99 ( 1H, t, J = 8. 0 Hz ), 7.77 ( 1H, t, J = 6. 8 Hz )

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2,4-difluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Eisai Co., Ltd.; EP1380576; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 68322-84-9, 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 68322-84-9 as follows.

EXAMPLE 7 Preparation of 3-[(2-Fluoro-5-(trifluoromethyl)phenyl]ethynyl]aniline A multinecked flash as described in Example 1 was charged with 4.93 g (0.020 mol) of 3-bromo-4-fluorobenzotrifluoride, 75 ml of dried, degassed triethylamine, 2.34 g (0.020 mol) of 3-aminophenylacetylene, 0.06 g (0.08 mmol) of bis(triphenylphosphine) palladium II chloride, 0.118 g (0.45 mmol) of triphenylphosphine, and 0.06 g (0.31 mmol) of cuprous iodide. The reaction mixture was heated at 70 C. for 40 hours at which point gas chromatography showed the reaction to be complete. The product mixture was cooled to room temperature and diluted with 75 ml of ether. Filtration of the insoluble hydrobromide salt followed by concentration of the filtrate gave the crude product (5.5 g, 89%) as an orange liquid. Short path distillation of the crude product under reduced pressure gave 4.05 g (0.014 mol, 70% yield) of the product as a yellow solid.

According to the analysis of related databases, 68322-84-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; National Starch and Chemical Investment Holding Corporation; US5107026; (1992); A;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, 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. Safety of 1,4-Dibromo-2,5-difluorobenzene

Under a nitrogen atmosphere, 200 ml Schlenk reaction vessel, 1, 4 – dibromo – 2, 5 – difluorobenzene (wako pure medicine industry) was added 80 ml (22.0mmol) (dehydration grade) and THF 5.98 g. The solution was cooled to 0 C, ethyl magnesium chloride (sigma-Aldrich -, 2.0M) 13.0 ml of the solution were dropped THF (26.0mmol). The mixture 10 minutes at 0 C aged. The resulting solution was added to copper (II) chloride (wako pure medicine industry) 3.89 g (29.0mmol), was stirred at room temperature for between 3. 40 ml water was added to stop the reaction container 1N hydrochloride. Extracted with toluene, the organic phase was washed with brine, dried over anhydrous sodium sulfate. Concentration under reduced pressure, the residue obtained by removing the low-boiling component from the eluent used 4, 4 ‘- dibromo – 2, 2′, 5, 5’ – 2.98 g (71% yield) of a pale yellow solid obtained tetra- fluoro biphenyl.

The synthetic route of 1,4-Dibromo-2,5-difluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TOSOH CORPORATION; MIYASHITA, MASATO; WATANABE, MASATO; (24 pag.)JP2017/160156; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 13194-73-5,Some common heterocyclic compound, 13194-73-5, name is 3,5-Dibromo-4-methylaniline, molecular formula is C7H7Br2N, 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 1 Synthesis of Compound M1 (Step (1a)) Under an argon gas atmosphere, 3,5-dibromo-4-methylaniline (47.0 g, 177 mmol), 35 wt % hydrochloric acid (111 ml) and ion exchanged water (111 ml) were mixed in a 1000 ml flask and cooled in an ice bath, and a solution prepared by dissolving sodium nitrite (12.9 g, 186 mmol) in ion exchanged water (about 130 ml) was dropped into the cooled mixture over a period of about 30 minutes. After completion of dropping, the mixture was stirred at room temperature for about 1 hour, then, cooled in an ice bath again, then, a solution prepared by dissolving potassium iodide (30.9 g, 186 mmol) in ion exchanged water (about 130 ml) was dropped into the cooled mixture over a period of 30 minutes. After completion of dropping, the mixture was stirred at room temperature for about 3 hours, then, added slowly to a separately prepared 10 wt % sodium hydrogen carbonate aqueous solution (about 1200 ml) while stirring. Ethyl acetate (about 1000 ml) was added and extraction was performed, the organic layer was washed with a 10 wt % sodium sulfite aqueous solution (about 450 ml), dried over anhydrous magnesium sulfate (50 g), filtrated, and the filtrate was concentrated to obtain a coarse product (77 g). The above-described coarse product was dissolved in acetone (750 ml), activated carbon (10 g) was added and stirred, then, the mixture was filtrated, and the filtrate was concentrated. It was again dissolved in acetone (750 ml), activated carbon (20 g) was added and stirred, then, the mixture was filtrated, and the filtrate was concentrated, and the deposited solid was dried under reduced pressure to obtain a yellow-brown solid (about 50 g). The resultant solid was dissolved in hexane, and ethanol was added to the solution to cause crystallization, and the resultant crystal was filtrated, and dried under reduced pressure, to obtain an intermediate 2,6-dibromo-4-iodotoluene (28.4 g, yield 43%, compound M1a) as a white crystal. 1H-NMR (300 MHz, CDCl3) delta (ppm)=2.51 (s, 3H), 7.83 (s, 2H)

The synthetic route of 13194-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; US2011/272686; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 67567-26-4, A common heterocyclic compound, 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, molecular formula is C6H4BrF2N, 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 3((1R)-1-{3,5-DIFLUORO-4-[(METHYLSULFONYL)AMINO]PHENYL}ETHYL)-6-(TRIFLUORO-METHYL)QUINOLINE-2-CARBOXAMIDE 3A) N-(4-BROMO-2,6-DIFLUOROPHENYL)METHANESULFONAMIDE To a solution of 4-bromo-2,6-difluoroaniline (3.0 g, 14.4 mmol) in pyridine (20 ml) was added methanesulfonyl chloride (2.23 ml, 28.8 mmol) at room temperature. Then the mixture was stirred at 50 C. for 6 hours. After cooing to room temperature, the mixture was concentrated in vacuo. The resulting residue was dissolved in THF (40 ml). To this solution was added 2M sodium hydroxide aqueous solution (40 ml) and the reaction was stirred at room temperature for 4 hours. The mixture was acidified with 2M HCl aqueous solution and extracted with EtOAc. The organic layer was washed with 2M HCl aqueous solution and brine, dried over sodium sulfate and concentrated in vacuo, to give the title compound (4.05 g, 98%) as an orange solid.1H NMR (270 MHz, CDCl3) delta 3.22 (3H, s), 6.08 (1H, br s), 7.17-7.24 (2H, m).MS (ESI) m/z 286 (M+H)+, 284 (M-H)-.

The synthetic route of 67567-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; RENOVIS, INC.; US2012/88746; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 65896-11-9, name is 2-Bromo-6-fluoroaniline, 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 65896-11-9, Quality Control of 2-Bromo-6-fluoroaniline

[0676] 2-Propylzinc bromide (0.50 M in THF, 16 mL, 7.9 mmol, Sigma-Aldrich Corporation, St. Louis, MO, USA) was added to a stirred mixture of 2-bromo-6-fluoroaniline (1.00 g, 5.26 mmol, Acros, Geel, Belgium), palladium (II) acetate (0.059 g, 0.263 mmol), and 2-dicyclohexylphosphino-2′,6′-dimethylamino-1,1′-biphenyl (0.230 g, 0.526 mmol, Strem Chemicals, Newburyport, MA) in THF (10 mL), and the resulting mixture was stirred under Ar(g) in a sealed vial at rt for 3 h. The reaction mixture was then diluted with satd. aq. ammonium chloride and extracted with EtOAc. The organic extract was then washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, eluent: 0-25% EtOAc in heptane) gave 2-fluoro-6-isopropylaniline as a yellow oil (Intermediate I-26, 618 mg, 4.03 mmol, 77 % yield).1H NMR (400 MHz, CDCl3) d ppm 6.92 (1H, d, J=7.88 Hz) 6.86 (1H, ddd, J=10.73, 8.14, 1.24 Hz) 6.69 (1H, td, J=7.88, 5.60 Hz) 3.70 (2 H, br s) 2.92 (1H, spt, J=6.84 Hz) 1.26 (6 H, d, J=6.84 Hz). m/z (ESI, +ve ion): 154.1 (M+H)+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; AMGEN INC.; ALLEN, John Gordon; ALLEN, Jennifer Rebecca; MINATTI, Ana Elena; XUE, Qiufen; WURZ, Ryan Paul; TEGLEY, Christopher M.; PICKRELL, Alexander J.; NGUYEN, Thomas T.; MA, Vu Van; LOPEZ, Patricia; LIU, Longbin; KOPECKY, David John; FROHN, Michael J.; CHEN, Ning; CHEN, Jian Jeffrey; SIEGMUND, Aaron C.; AMEGADZIE, Albert; TAMAYO, Nuria A.; BOOKER, Shon; GOODMAN, Clifford; WALTON, Mary; NISHIMURA, Nobuko; SHIN, Youngsook; LOW, Jonathan D.; CEE, Victor J.; REED, Anthony B.; WANG, Hui-Ling; LANMAN, Brian Alan; (738 pag.)WO2019/213516; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary