Author: Jessica.F

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. 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-4-(tert-butyl)aniline

2-Bromo-4-tert-butyl-phenylamine (162 g, 0.71 mol) was added dropwise to H2SO4 (410 mL) at room temperature to yield a clear solution. This clear solution was then cooled down to -5 to -10 C. A solution of KNO3 (82.5 g, 0.82 mol) in H2SO4 (410 mL) was added dropwise while the temperature was maintained between -5 to -10 C. Upon completion, the reaction mixture was poured into ice/water and extracted with EtOAc. The combined organic layers were washed with 5% Na2CO3 and brine, dried over Na2SO4 and concentrated. The residue was purified by a column chromatography (EtOAc/petroleum ether 1/10) to give 2-bromo-4-tert-butyl-5-nitro-phenylamine as a yellow solid (152 g, 78%).

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; Vertex Pharmaceuticals Incorporated; US2012/309758; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 7073-94-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 7073-94-1 name is 1-Bromo-2-isopropylbenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Add 4.8 mmol (117 mg) of magnesium metal to a 25 mL Shrek bottle, 10 mL of tetrahydrofuran and 4 mmol (0.62 mL) of 2-isopropylbromobenzene, Stir at room temperature for 1h, Let stand. In a 250 mL three-necked flask, add 0.4 mmol (232 mg) of the compound represented by formula (XIa) and 80 mL of tetrahydrofuran. Cool to -20 , The fresh Grignard reagent was transferred to a 25 mL constant pressure dropping funnel and slowly added to the reaction system. After the dropping was completed, the system was transferred to room temperature and the reaction was continued for 12 h. After the reaction was completed, a saturated ammonium chloride solution was added to quench it. Extract the aqueous phase with ethyl acetate, The organic phases were combined, washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was spin-dried column chromatography (silica gel 100-200 mesh, eluent: dichloromethane / ethyl acetate = 10/1 to 8/1) to obtain 186 mg of the compound represented by formula (IIIc) in a yield of 44%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-isopropylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; Tsinghua University; Wang Meixiang; Shi Tanhao; Guo Qinghui; Tong Shuo; (35 pag.)CN110372468; (2019); 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 1647-23-0 as follows. name: 1-Bromo-3,3-dimethylbutane

Step 5. 5-amino-6-chloro-N-{[1-(3,3-dimethylbutyl)piperidin-4-yl]methyl}-2-ethylimidazo[1,2-a]pyridine-8-carboxamide To a stirred mixture of 5-amino-6-chloro-2-ethyl-N-(piperidin-4-ylmethyl)imidazo [1,2-a]pyridine-8-carboxamide (EXAMPLE 28, Step 4, 450 mg, 1.34 mmol) and 1-bromo-3,3-dimethylbutane (606 mg, 3.35 mmol) in N,N-dimethylformamide (6 mL) were added potassium carbonate (648 mg, 4.69 mmol) and sodium iodide (502 mg, 3.35 mmol). After stirring at 90 C. for 42 h, the reaction mixture was cooled and evaporated. The residue was diluted with dichloromethane (30 mL) and water (20 mL). The water phase was extracted with dichloromethane (2*30 mL). The combined extract was washed with brine, dried over magnesium sulfate, and concentrated. Flash chromatography (NH-silica gel) of the residue eluding with hexane/ethyl acetate (1:1 to 1:2) afforded a brown solid (296 mg), which was recrystallized from ethyl acetate to give 191 mg (34%) of the title compound as a pale brown solid. MS (ESI) m/z: 420 (M+H)+, 418 (M-H)-. m.p. (TG/DTA): 234 C. IR (KBr) nu: 3136, 2947, 1636, 1607, 1558 cm-1. 1H-NMR (CDCl3) delta: 0.89 (9H, s), 1.36 (3H, t, J=7.5 Hz), 1.98-1.36 (9H, m), 2.37-2.26 (2H, m), 2.83 (2H, q, J=7.5 Hz), 3.02-2.92 (2H, m), 3.45 (2H, t, J=6.2 Hz), 4.96 (2H, bsv), 7.12 (1H, s), 8.20 (1H, s), 10.17 (1H, bs). Anal. Calcd. for C22H34ClN5O: C, 62.91; H, 8.16; N, 16.68. Found: C, 62.71; H, 8.20; N, 16.62.

According to the analysis of related databases, 1647-23-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Uchida, Chikara; Noguchi, Hirohide; Stobie, Alan; Gymer, Geoffrey; Fenwick, David; US2003/92699; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1198171-18-4, name is 1-Bromo-2-(difluoromethyl)-4-fluorobenzene, 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 1198171-18-4, Recommanded Product: 1198171-18-4

Step 2) Preparation of2-(difluoromethyl)-4-fluorobenzaldehyde (78): Isopropyl magnesium bromide (30 mL,l M in THF, 30 mmol) was added dropwise to an ice-cooled solution of l-bromo-2-(difluoromethyl)-4-fluorobenzene (77; 6g,26.7mmol) in THF (100 mL). The reaction mixture was then allowed to warm to room temperature and stirred for 3 hr. Dimethylformamide (3.5 mL, 45.2 mmol) was added and the reaction stirred for 3 hr. Water was added and the mixture was extracted with ethyl acetate. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography to afford 2- (difluoromethyl)-4-fluorobenzaldehyde 78 (3.2g, 68%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-(difluoromethyl)-4-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; WO2009/146358; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 5003-71-4, name is 3-Bromopropan-1-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 5003-71-4, Product Details of 5003-71-4

In a solution of 3-bromopropan-1 -amine hydrobromide (1.00 g, 0.46 mmol) in THE (40m1) trimethylamine (imI, 0.58 mmol) is added and the resulting reaction mixture isstirred for half an hour, then catalytic amount of 2-methylaminopyridine is added into the reaction mixture. Einally, in ice cold condition 1.23 ml of Boc anhydride is also added into it, in a dropwise manner and the reaction mixture is stirred for overnight. Now slowly, the reaction mixture is quenched with ammonium chloride and extracted with ethyl acetate. The combined organic phase is washed with brine and finally dried over anhydrousNa2504. The crude product is further purified by flash chromatography by using 60-1 20mesh silica gel and ethyl acetate/hexane as mobile phase. The product tert-butyl (3-bromopropyl)carbamate is obtained as a yellowish solid upon cooling at 4 00 (Yield: 0.9 g(83%))

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromopropan-1-amine hydrobromide, and friends who are interested can also refer to it.

Reference:
Patent; SHIV NADAR UNIVERSITY; ROY, Gouriprasanna; BANERJEE, Mainak; KARRI, Ramesh; CHALANA, Ashish; DAS, Ranajit; (61 pag.)WO2017/168451; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1435-51-4, 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. 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 1,3-dibromo-5-fluorobenzene (LXI) (2.0 g, 7.88 mmol) in toluene (20 ml) was added potassium t-butoxide (2.65 g, 23 6 mmol) and 1-methylpiperazine (1.75 mL, 15.8 mmol). The reaction was heated at 105 C. overnight. The toluene was removed under vacuum and the residue was dissolved in water and extracted with EtOAc. The organic phase was separated, washed with brine, dried over MgSO4 and concentrated to dryness. The crude product was purified on a silica gel column (1:99 MeOH:CHCl3?7:93 MeOH:CHCl3) to produce 1-(3-bromo-5-fluorophenyl)-4-methylpiperazine (LXII) as an orange oil (800 mg, 2.93 mmol, 37.2% yield). 1H NMR (DMSO-d6, 500 MHz) delta ppm 2.20 (s, 3H), 2.39 (t, J=5 Hz, 4H), 3.33 (t, J=5 Hz, 4H), 6.74-6.81 (m, 2H), 6.91 (s, 1H); ESIMS found for C11H14BrFN2 m/z 273 (M+H).

The synthetic route of 1,3-Dibromo-5-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samumed, LLC; Hood, John; Kumar KC, Sunil; Wallace, David Mark; US2013/296302; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, 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 1435-51-4, category: bromides-buliding-blocks

A solution of l,3-dibromo-5-fluorobenzene (0.50 g, 1.99 mmol), 3-thiopheneboronic acid (0.254 g, 1.99 mmol), 2.0 M aqueous Sodium carbonate (1.99 niL, 3.97 mmol) and Pd(PPh3)4 (115 mg, 0.10 mmol) in toluene (9.2 mL) and ethanol (2.4 mL), was heated at 1000C for 1.5 hours by microwave. The product mixture was diluted with EtOAc (100 mL) filtered, washed with water (50 mL), brine (50 mL), dried with Na2SO4 and concentrated. Flash chromatography (2% EtOAc in hexane, silica) resulted in 400 mg of pure product as a clear oil.

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; ARENA PHARMACEUTICALS, INC.; WO2006/65600; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 6627-78-7,Some common heterocyclic compound, 6627-78-7, name is 1-Bromo-4-methylnaphthalene, molecular formula is C11H9Br, 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 mixture of 1-bromo-4-methylnaphthalene (1.0 g, 4.52 mmol, 1.0 eq), tert-butyl 4- (4,4,5, 5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-l(2H)-carboxylate (2.1 g, 6.78 mmol, 1.5 eq) and Na2C03 (1.43 g, 13.56 mmol, 3.0 eq) in a mixture of 1,2-DME (15 mL) and water (5 mL) was purged with nitrogen for 15 min. Pd(dppf)Cl2 DCM (0.36 g, 0.45 mmol, 0.1 eq) was added to the reaction mixture and was stirred under nitrogen atmosphere, at 80 C for 2 h. After complete consumption of starting material, the mixture was cooled to ambient temperature and partitioned between water and ethyl acetate. The organic extract was separated and the aqueous extract was again extracted with ethyl acetate. The combined organic extract was washed with brine, dried over anhydrous Na2S04, filtered and solvents evaporated from the filtrate under reduced pressure to obtain a crude product, which was purified by flash chromatography on silica gel, 230-400 mesh, using gradient of ethyl acetate in hexanes as eluent to obtain tert-butyl 4-(4-methylnaphthalen-l-yl)-3,6-dihydropyridine-l(2H)-carboxylate. LCMS: Purity 82.42%. MS calculated for [M]323.44 and found [M+H] +324.20

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-methylnaphthalene, its application will become more common.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; PANDEY, Anjali; BOWERS, Simeon; BARTA, Thomas E.; BOURNE, Jonathan William; (208 pag.)WO2017/147328; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 627871-16-3, These common heterocyclic compound, 627871-16-3, name is 5-Bromo-4-fluoro-2-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.

In a 250 mL round-bottomed flask was placed 4-(pyridin-2-ylmethoxy)benzoic acid (3.4 g, 14.7) in DCM (50 mL) to give a suspension. To the solution, SOCl2 (22.29 mL, 305.37 mmol) was added. The mixture was stirred at RT overnight. Concentration removed SOCl2 and DCM to give crude 4-(pyridin-2-ylmethoxy)benzoyl chloride. To the residue was added 5-bromo-4-fluoro-2-methylaniline (3.0 g, 14.70 mmol), DIPEA (6.42 mL, 36.76 mmol), and DCM (60 mL) to give a black solution. The reaction was stirred at RT overnight. Concentration under reduced pressure gave the crude product, which was purified by ISCOMPLC (0-6% MeOH/DCM) to give the title compound.

Statistics shows that 5-Bromo-4-fluoro-2-methylaniline is playing an increasingly important role. we look forward to future research findings about 627871-16-3.

Reference:
Article; Bodnarchuk, Michael S.; Brassil, Patrick; Dakin, Les; Daly, Kevin; Godin, Robert; Hattersley, Maureen M.; Hird, Alexander W.; Janetka, James W.; John Russell, Daniel; Redmond, Sean; Su, Qibin; Yang, Bin; Zheng, Xiaolan; Bioorganic and medicinal chemistry; vol. 28; 2; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 327-51-5, A common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, molecular formula is C6H2Br2F2, 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.

(1380) [00444] Into a 50-mL round-bottom flask that was purged and maintained under an inert atmosphere of nitrogen was added 1 ,4-dibromo-2,5-difiuorobenzene (1.50 g, 5.52 mmol), tert- butyl 4-(tetramethyl-l,3,2-dioxaborolan-2-yl)-l,2,3,6-tetrahydropyridine-l-carboxylate (1.88 g, 6.06 mmol), potassium carbonate (2.28 g, 16.5 mmol), Pd(dppf)Cb’CH2Cl2 (400 mg, 0.49 mmol), DMF (20 mL) and H2O (2 mL). The reaction mixture was stirred for 2 h at 50 C and then cooled and quenched with water (20 mL). The resulting solution was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL). The organic layer was then concentrated in vacuo. The resulting crude product was purified by FCC eiuting with petroleum ether/ethyl acetate (5: 1) to afford fer/-butyl 4-(4-bromo- 2,5-difluorophenyl)-3,6-dihydropyridine-l(2 )-carboxylate (1.5 g, 73%). H-NMR (300 M ( DO delta ppm 7.21-7.29 (m, 1H), 6.93-7.08 (m, 1H), 5.81-5.61 (m, 1H), 4.01-4.14 (m, 2H), 3.62 (t, J – 5,7 Hz, 2H), 2.48-2.51 (m, 2H), 1 ,50 (s, 9H).

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORMA THERAPEUTICS, INC.; GUERIN, David Joseph; BAIR, Kenneth W.; CARAVELLA, Justin A.; IOANNIDIS, Stephanos; LANCIA JR., David R.; LI, Hongbin; MISCHKE, Steven; NG, Pui Yee; RICHARD, David; SCHILLER, Shawn E. R.; SHELEKHIN, Tatiana; WANG, Zhongguo; (365 pag.)WO2017/139778; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary