Category: bromides-buliding-blocks

Reference of 698-00-0, 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. 698-00-0, name is 2-Bromo-N,N-dimethylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A dry Schlenk tube under argon atmosphere was charged with the 2-bromo-N,Ndimethylaniline (1.99 g, 10 mmol) in degassed THF (15 mL). The solution was cooled at -78 C and n-BuLi (2,4 M in THF, 1.1 eq.) was added. The mixture was stirred for 30 min at -78 C and then, at 0 C for 15 minutes. Then PPh2Cl (1.93 mL, 10.5 mmol) neat was added at -78 C under an argon atmosphere. The white solution was filtered on a pad of celite, the solid was washed with pentane (20 mL), ether (20 mL) and CH2Cl2 (20 mL). 2-(diphenylphosphino)-N,N-dimethylaniline was obtained after purification by flash chromatography on silica gel (eluent : AcOEt / cyclohexane 10 / 90) as a white solid (1,67 g, 56%).

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-Bromo-N,N-dimethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Pagnoux-Ozherelyeva, Anastassiya; Bolien, David; Gaillard, Sylvain; Peudru, Flavie; Lohier, Jean-Francois; Whitby, Richard J.; Renaud, Jean-Luc; Journal of Organometallic Chemistry; vol. 774; (2014); p. 35 – 42;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 1798-85-2, name is 1-Bromo-3-cyclopropylbenzene, molecular formula is C9H9Br, 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. COA of Formula: C9H9Br

A mixture of N- (4- (methylsulfonyl ) benzyl) -3, 4-dihydro-2H- (3811) 1 , 4-benzoxazine-7-carboxamide (0.028 g, 0.08 mmol), l-bromo-3- cyclopropylbenzene (32 mg, 0.160 mmol), RuPhos Pd Gl (5.83 mg, 8.00 mumol) , RuPhos (3.73 mg, 8.00 muiotatauiotaomicron) , NaOtBu (0.023 g, 0.240 mmol) and DME (1 mL) was heated at 130 C for 2 h under (3812) microwave irradiation. The reaction mixture was diluted with AcOEt (3 mL) and quenched with H20 (1 mL) , and stirred for 2 min. The organic layer was separated and then the aqueous layer was extracted with EtOAc (2 mL) . The combined organic layer was evaporated by blowing away with the air at 60 C. The residue was purified by preparative HPLC (Actus Triart C18, eluted with MeCN/10 mM NH4HCO3 aq. 5:95?100:0). Pure fractions were combined and concentxated by blowing away with the air at 60C to afford the title compound (19.8 mg, 0.0428 mmol, 54%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1798-85-2, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; YAMAMOTO, Satoshi; SHIRAI, Junya; KONO, Mitsunori; SHIOKAWA, Zenyu; YUKAWA, Tomoya; IMADA, Takashi; NEGORO, Nobuyuki; ODA, Tsuneo; SASAKI, Satoshi; NARA, Yoshi; SUZUKI, Shinkichi; SATO, Ayumu; ISHII, Naoki; SHIBUYA, Akito; NAKAGAWA, Yasuo; COLE, Derek; GIBSON, Tony; IVETAC, Anthony; SWANN, Steve; TYHONAS, John; (472 pag.)WO2018/30550; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 18648-66-3, name is 2-(4-Bromophenyl)-1,1-diphenylethylene, 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 18648-66-3, Safety of 2-(4-Bromophenyl)-1,1-diphenylethylene

theTriphenylethylene bromide (3.35g,10.0mmol) dissolved in 20ml of tetrahydrofuran,cool down to -78 C, slowly drop wise added 2.5M n-butyllithium solution(4.0ml,10.0ml). After the addition was complete for 2 h, N, N-dimethylformamide(1.46g,20.0ml)was added, naturally heated to room temperature and kept thereaction for 24 h. The reaction was terminated, extraction was carried out withwater,after organic phase was dried over anhydrous sodium sulfate and dried invacuo on a rotary evaporator to give the crude product. The product waspurified by silica gel column chromatography; the eluent was a mixed solvent ofdichloromethane and n-hexane with volume ratio of 3:1. Pure product as a whitesolid, 3.3 g (yield 81%).

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

Reference:
Patent; Sun Yat-sen University; Ma, ChunPing; Chi, ZhenGuo; Zhou, Xie; Zhang, Yi; Liu, SiWei; Xu, JiaRui; (14 pag.)CN103804318; (2016); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 39478-78-9, These common heterocyclic compound, 39478-78-9, name is 5-Bromo-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.

To a solution of 5-bromo-2-methylaniline (5.0 g, 27 mmol) in conc.H2S04 (40 mL) was added KN03 (2.7 g, 27 mmol) in portions and kept the internal temperature below 5 C. The resulting mixture stirred for 2 hrs under ice bath. The resulting mixture was poured into icewater and stirred for 10 mm. The mixture was filtered and the cake was washed with water(100 mL). The cake was purified by column chromatography (PE: EtOAc from 20: ito 10: 1)to give the title compound (3.1 g, yield 50%).0421 1H NMR (300 MHz, CDCI3): oe 7.88 (s, IH), 6.91 (s, 1H), 4.25 (brs, 2H), 2.16 (s, 3H).

Statistics shows that 5-Bromo-2-methylaniline is playing an increasingly important role. we look forward to future research findings about 39478-78-9.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R & D COMPANY LIMITED; DING, Xiao; JIN, Yun; LIU, Qian; REN, Feng; SANG, Yingxia; STASI, Luigi Piero; WAN, Zehong; WANG, Hailong; XING, Weiqiang; ZHAN, Yang; ZHAO, Baowei; (573 pag.)WO2017/12576; (2017); A1;,
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.

Method 6 4-Bromo-2,5-difluorobenzaldehyde To 1,4-dibromo-2,5-difluorobenzene (10.28 g, 37.81 mmol) in tetrahydrofuran (80 mL) at -40 C. was isopropylmagnesium chloride lithium chloride complex (29.1 mL, 37.81 mmol) added dropwise. After 1 h at -40 C. was N,N-dimethylformamide (58 mL, 756 mmol) added and the mixture was stirred for 30 minutes at -40 C. NH4Cl (2M, aq, 100 mL) was added and the mixture was extracted with ethyl acetate. The organic phase was dried with MgSO4 and concentrated to give 4-bromo-2,5-difluorobenzaldehyde (6.20 g, 74%) as a solid. 1H NMR (500 MHz, CHLOROFORM-d) delta ppm 10.28 (d, 1H) 7.61 (dd, 1H) 7.48 (dd, 1 H).

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

Reference:
Patent; ASTRAZENECA AB; US2010/267723; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 941-37-7, 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 941-37-7 as follows.

To 100g of 1-bromo-3, 5-dimethyl adamantane and 86g of urea, adding 80ml of 80wt% formic acid, heating to 80C and holding for 3 hours. Cooling to the room temperature and adding 75ml of 85% phosphoric acid to hydrolyze at 80C for 1 hour. Adjusting with 10% potassium hydroxide aqueous solution to a pH of 12. Extracting with toluene twice, combining the organic layers and washing with water. Concentrating under reduced pressure to yield a limpid yellow solution as 1-amino-3,5-dimethyl adamantane crude. To the crude, adding 150ml of ethanol and concentrated hydrochloric acid, heating to dissolve and crystallizing to yield a white solid. Drying the solid and re-crystallizing with ethanol to yield 61.0g of pure Memantine Hydrochloride. The yield is 68.8% (GC 99.5%). 1HNMR (CDCl3, 400MHZ): delta0.833 (6H, singlet), 1.156 (2H, quartet), 1.328 (4H, quartet), 1.683(4H, quartet), 1.869 (2H, broad signal), 2.179 (1H, broad signal), 8.28 (3H, broad signal). MS (Q-Tof micro, ESI+): 179(M+), 164, 122, 108, 93 and 55. Element Analysis (C12H21N.HCl): actual results (calculated value%): C 66.77 (66.80), H 10.40 (10.28), N 6.48(6.49) and Cl 16.39(16.43)

According to the analysis of related databases, 941-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Institute of Pharmaceutical Industry; Zhejiang Kangyu Pharmaceutical Co., Ltd.; EP1674446; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 5469-19-2, name is 1-Bromo-2,4,5-trimethylbenzene, molecular formula is C9H11Br, 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-Bromo-2,4,5-trimethylbenzene

d. N,N’-(4,4′-(cyclohexane-1 ,1 -diyl)bis(4, 1 -phenylene))bis(2,4,5-trimethyl- N-(2,4,5-trimethylphenyl)aniline) In a dry box, 4,4′-(cyclohexane-1 , 1 -diyl)dianiline (6.75 g, 25.09 mmol), 1 – bromo-2,4,5-trimethylbenzene (21 .19 g, 105.36 mmol), tris(tert- butyl)phosphine (0.41 g, 2.01 mmol) and Pd2(DBA)3 (0.92 g, 1 .00 mmol) were combined in round bottom flask and dissolved in 450 ml of dry toluene. The solution was stirred for a minute and followed by sodium tert- butoxide (10.61 g, 1 10.38 mmol) and 50 ml of dry toluene. A heating mantle was added and the reaction heated to 80C for 18 hour. The reaction mixture was then cooled to room temperature and filtered, washing with chloroform. The solvent was removed by rotary evaporation and the residue was purified further by silica gel column chromatography using a gradient of chloroform in hexanes (0-25%). The product containing fractions were collected and combined. The solvent was removed by rotary evaporation. The crude product was dissolved in DCM (100 ml_) and precipitated into methanol (700 ml_) to give 1 7.47 g (94%) product as a white powder. 1 H NMR (CDCI3) is consistent with structure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5469-19-2, its application will become more common.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WANG, Ying; WU, Weishi; DOBBS, Kerwin, D.; WO2011/49904; (2011); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1647-23-0, The chemical industry reduces the impact on the environment during synthesis 1647-23-0, name is 1-Bromo-3,3-dimethylbutane, I believe this compound will play a more active role in future production and life.

6-t-butyll-8-H-pteridinone (50 mg, 0.21 mmol, from preparative example 3) in 1 mL DMF was added 60 mg potasium carbonate and 1.5equiv. of 1-bromo-3,3-dimethylbutane. The reaction mixture was stirred at rt for 4 hours. The solid was filtered. The filtrate was concentrated. The residue was purified by column chromotagraphy (silica gel, 4:1 hexanes:ethyl acetate) to give 51 mg desired product. LC-MS [M+1]=319.

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-3,3-dimethylbutane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhu, Song; US2005/250779; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, 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. Quality Control of 1-Bromo-2,4,5-trifluorobenzene

In an oven-dried flask, dried halogen-group-containing compounds (2.3 equiv) were added to dry THF containing magnesium metal (Mg) (2.3 equiv, with glass pieces to activate the magnesium metal) at room temperature under nitrogen. The reaction mixture was stirred vigorously until Grignard generation occurred. The lactone (1 equiv dissolved in 40 mL of THF) was added dropwise to the Grignard reagent solution, and the mixture was stirred at room temperature for 16 h and monitored by TLC. The mixture was treated with saturated aqueous NH4Cl (20 mL) and then extracted with AcOEt (3¡Á10mL). The combined organic phases were dried over Na2SO4 and the solvent was removed by an evaporator. The residue was purified by silica-gel column chromatography (AcOEt/hexane). In another experiment, the ring-opening reactions of homoserine lactone with select Grignard reagents were carried out using 2.7 equiv ArMgBr at r.t. and 50C for 2 h.

The synthetic route of 327-52-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guendo?du, Oezlem; Turhan, P?nar; Koese, Aytekin; Altunda?, Ramazan; Kara, Yunus; Tetrahedron Asymmetry; vol. 28; 9; (2017); p. 1163 – 1168;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 61613-22-7, A common heterocyclic compound, 61613-22-7, name is 2-Bromo-N-phenylaniline, molecular formula is C12H10BrN, 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.

Under an Ar atmosphere, to a 500 ml, three-neck flask, Compound C (5.00 g) was put and dissolved in dehydrated THF (100 ml), and nBuLi (1.6 M in hexane, 12.6 ml) was added dropwise thereto at about -78 C. After stirring at about -78 C. for about 1 hour, a THF solution (100 ml) of B (7.01 g) was added dropwise thereto, followed by stirring for about 16 hours while gradually increasing the temperature to ambient temperature. Water was added to the resultant product, and an organic layer was extracted with CH2Cl2, separated, and dried with MgSO4. Solvents were removed by distillation under a reduced pressure. The crude product thus obtained was dissolved in toluene (100 ml), and pTsOH (11.5 g) was added thereto, followed by heating and stirring at about 80 C. for about 6 hours. After the reaction, a precipitate thus produced was obtained by filtering and separated by recrystallization to obtain 6.24 g (yield 62%) of Intermediate D. The molecular weight of Intermediate D measured by FAB-MS was 499.

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; SAMSUNG DISPLAY CO., LTD.; SAKAMOTO, Naoya; AKASHI, Nobutaka; (46 pag.)US2020/20866; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary