Month: June 2021

Reference of 583-75-5, A common heterocyclic compound, 583-75-5, name is 4-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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 4-bromo-2-methylaniline (1 g, 5.37 mmol,) in 1,4-dioxane (11 mL) and H2O (4 mL), at r. t. , were added Et3N (2.7 mL, 1.2 eq) and BOC20 (4.2 g, 1.2 eq). The reaction mixture was stirred at r. t. for 96 hr. Sat. aq. NH4CI and EtOAc (20 mL) were added and the phases were separated. The aqueous layer was further extracted with EtOAc (2X20 mL). The combined organic extracts were dried over anh. NA2SO4, the solids were filtered and the solvent evaporated. The residue was purified by SCX Column (Eluents : CH2CI2, MeOH and NH3 (0.5 M in MEOH)) to give the title compound as a white solid (1.22 g, 79%). NMR (‘H, DMSO-D6) : 8 8.55 (s, 1H), 7.35 (m, 1H), 7.28 (m, 2H), 2.17 (s, 3H), 1.44 (s, 9H). MS (m/z) : 230 [MH-TBU] + ; 186 [MH-BOC] +.

The synthetic route of 583-75-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SB PHARMCO PUERTO RICO INC; NEUROCRINE BIOSCIENCES INC; GLAXO GROUP LIMITED; WO2004/62665; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1003-99-2, name is 2-Bromo-5-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 1003-99-2, COA of Formula: C6H5BrFN

General procedure: Method I. Compounds 1a-1e and 3b were synthesized using a modified procedure.1 Substituted aniline (1.0 equiv.) was added to a round-bottom flask. The flask was fitted with a rubber septum and purged with nitrogen gas, and acetic anhydride (1M in CH2Cl2, 1.1 equiv.) was added at room temperature. The reaction was refluxed overnight and monitored by TLC. Upon completion the reaction mixture was quenched with H2O. The resulting mixture was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anh. Na2SO4, filtered, then concentrated in vacuo to give the product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Article; Lasing, Thitiya; Phumee, Atchara; Siriyasatien, Padet; Chitchak, Kantima; Vanalabhpatana, Parichatr; Mak, Kit-Kay; Hee Ng, Chew; Vilaivan, Tirayut; Khotavivattana, Tanatorn; Bioorganic and Medicinal Chemistry; vol. 28; 1; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 10016-52-1, name is 2,8-Dibromodibenzo[b,d]furan, 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. Application In Synthesis of 2,8-Dibromodibenzo[b,d]furan

To a 250 ml three-mouth bottle adding 5.04g (0.022 muM) precursor 1 (through the implementation of example one preparation) and 3.26g (0.01 muM) 2, 8 – dibromodiphenyl benzofuran, the mixture thus obtained is VI, VI is added to the mixture in the 40g toluene. Opening stirring, system for the picture and the turbid, N2Replacement system 10min. In the system by adding 2.8g (0.025 muM) tert-butanolate, 0.18g (2 × 10-4Mol) Pd2(Dba)3And 0.12g (4 × 10-4Mol) tri-butyl phosphine four fluoroborates, 80 C reaction 8 hours. The said technological, cooling to 20 – 25 C, the reaction liquid filtration, filtrate directly filtering of the silica gel column, eluting with toluene, the solvent under reduced pressure, to be brownish red color oil of 6.5g. In the above-mentioned crude product in adding toluene and hexane recrystallization (mass ratio of 2:1), vacuum drying oven drying 3h, gain the light yellow powder 2.5g, yield: 40.2%.

The synthetic route of 2,8-Dibromodibenzo[b,d]furan has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CECEP Wanrun Co., Ltd.; Ren Huicai; Pang Maoyin; Yang Fushan; Tian Shaozhen; Shi Rujin; Hu Baohua; (14 pag.)CN105153085; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 21120-91-2,Some common heterocyclic compound, 21120-91-2, name is 7-Bromobicyclo[4.2.0]octa-1,3,5-triene, molecular formula is C8H7Br, 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 rbf with magnetic stir bar was added aminophenol (1 g, 1 eq), THF (15 ml) and KOtBu (1.23 g, 1.2 eq). The mixture was allowed to stir for 1 hour at room temperature. Bromo BCB (1.68 g, 1 eq) was added in THF (15 ml). The reaction was capped and allowed to stir for 12 h at room temperature. Water (100 ml) was then added. Ethyl acetate (3×100 ml) was used to extract the product from the aqueous phase. The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was subjected to a column of silica gel using heptanes and ethyl acetate (9:1) as eluent to give product (892 mg, 46%) as a dark oil. (0077) 1H NMR (500 MHz, Chloroform-d) delta 7.32 (dt, J=6.6, 4.3 Hz, 1H), 7.28-7.23 (m, 2H), 7.18 (d, J=7.4 Hz, 1H), 6.86 (d, J=9.0 Hz, 2H), 6.69 (d, J=9.0 Hz, 2H), 5.59 (dd, J=4.3, 2.1 Hz, 1H), 3.66 (dd, J=14.1, 4.3 Hz, 1H), 3.46 (br s, 2H), 3.28 (d, J=14.1 Hz, 1H). 13C NMR (126 MHz, Chloroform-d) delta 151.04, 145.18, 142.64, 140.49, 129.73, 127.29, 123.47, 123.00, 116.48, 116.36, 74.89, 39.47. DSC Showed an exotherm peak temperature at 179 C at a scan rate of 10 C/min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Bromobicyclo[4.2.0]octa-1,3,5-triene, its application will become more common.

Reference:
Patent; Rohm and Haas Electronic Materials LLC; Hayes, Colin; Gallagher, Michael K.; Riener, Michelle; (10 pag.)US2019/169327; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 608-30-0, name is 2,6-Dibromoaniline, molecular formula is C6H5Br2N, 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: C6H5Br2N

In a 1 L three-necked flask, the raw material 2,6-dibromoaniline (25 g, 0.1 mol), iodobenzene (51 g, 0.25 mol), copper powder (7.0 g, 0.11 mol), potassium carbonate ( 34.5g, 0.25mol), o-dichlorobenzene (500mL), heated to 160 C under nitrogen protection, heat preservation reaction for 24 hours, cool to 25 C, suction filtration, 200g toluene rinse filter cake, collect filtrate, remove solvent The obtained crude product was purified by silica gel column chromatography. The eluent was petroleum ether: ethyl acetate=5:1, and the target product A01 was obtained in the form of 28.5 g, yield 70.7%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 608-30-0, its application will become more common.

Reference:
Patent; CECEP Wanrun Co., Ltd.; Sheng Lei; Wang Zheng; Li Yinhua; Gao Shukun; Hu Baohua; Hou Feifei; (19 pag.)CN108383847; (2018); A;,
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. 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, A new synthetic method of this compound is introduced below., Quality Control of 1,3-Dibromo-5-fluorobenzene

Ice bath, the 2M Isopropylmagnesium chloride (10 mL, 20 mmol) was dissolved in 5 mL of tetrahydrofuran, A solution of 1,3-dibromo-5-fluorobenzene 40a (4.0 g, 15.70 mmol) In tetrahydrofuran,Stirred for 2 hours, and then heated to 20 C reaction for 30 minutes. Cool down to 0 C,N, N-Dimethylformamide (2.5 mL, 31.50 mmol) was added dropwise,The reaction was stirred for 1.5 hours,The reaction was stirred at room temperature for 12 hours.The reaction was quenched by the addition of 20 mL of saturated ammonium chloride solution, extracted with ethyl acetate (50 mL of X3) and the organic phases were combined, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure and eluted with silica gel column chromatography eluent system B The resulting residue was purified to give the title product 3-bromo-5-fluorobenzaldehyde 40b (2.57 g, yellow liquid), yield: 81.0%.

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

Reference:
Patent; SHANGHAI HENGRUI PHARM CO LTD; JIANGSU HENGRUI MEDICINE CO LTD; Lyu, HEJUN; DONG, QING; FEI, HONGBO; JIANG, HONGJIAN; SONG, PENG; (114 pag.)CN103030646; (2016); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 444-14-4,Some common heterocyclic compound, 444-14-4, name is 2-Bromo-4,6-difluoroaniline, molecular formula is C6H4BrF2N, 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.

Dissolve 2-bromo-4,6-difluoroaniline (40 g, 192 mmol) in methyldisulfide (250 mL) and heat to 75 C under nitrogen. Add isoamyl nitrite (67 mL, 500 mmol) dropwise via an addition funnel trough a reflux condenser (-1 drop/sec). Large exotherm may occur if addition is too fast. After addition is complete, heat the reaction to 95 C for 1 hour and cool to room temperature and concentrate in vacuo. Purify dark brown residue via silica gel chromatography eluting with hexanes to yield 30.3 g of 1-bromo-3, 5- difluoro-2-methylsulfanyl-benzene (66%). Charge a flask with isopropyl magnesium chloride (145 mL, 2M in THF, 290 mmol) and dilute with tetrahydrofuran (150 mL) and heat to 40 C under nitrogen. Add 1-bromo-3, 5-difluoro-2-methylsulfanyl-benzene (28 g, 117 mmol) slowly over 5 minutes. After 30 minutes, cool the reaction to 0 C and add trimethylborate (46 mL, 410 mmol) diluted with tetrahydrofuran (100 mL) via an addition funnel over 5 minutes. Partition the resulting gelatinous mixture between methylene chloride and 1N HC1. Acidify the aqueous layer to pH-1 (if needed) and vigorously stir the biphasic mixture until all solids are dissolved. the organic layer. Dry over sodium sulfate, filter and concentrate. Triturate with hexanes and filter to yield 14.7 g (61 %) of the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4,6-difluoroaniline, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73204; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 6627-78-7, 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. 6627-78-7 name is 1-Bromo-4-methylnaphthalene, 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.

2.21 g (10 mmol) of compound V-2And 3.76 g (20 mmol) of B(i-PrO)3 dissolved in 14 mL of dry toluene and 7 mL of THF.Stir and cool to -30 C under nitrogen.Then, 6.25 mL (10 mmol) of a 1.6 M n-BuLi n-hexane solution was slowly added dropwise with a syringe.After the dropwise addition was completed, the reaction mixture was stirred at this temperature for 3 hours.Then stir at room temperature for another 3 hours.TLC tracking revealed that the reaction was complete.1 mL of concentrated hydrochloric acid was slowly added to the reaction mixture, and the mixture was stirred at room temperature for 1 hour.Then, it was poured into 200 mL of ice water, stirred, extracted with 50 mL of ×3CH2Cl2, and the combined phases were combined, washed with 100 mL of 5% brine, and dried over anhydrous sodium sulfate.The desiccant was removed by suction filtration, and the filtrate was evaporated to dryness on a rotary evaporator.Compound VI-2 was obtained.

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

Reference:
Patent; Foshan Sai Weisi Pharmaceutical Technology Co., Ltd.; Cai Ziyang; (9 pag.)CN108129453; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 50548-45-3, name is 1-Bromodibenzo[b,d]furan belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 50548-45-3

20 g (80 mmol) of dibenzofuran-1-boronic acid, 2.06 g(40.1 mmol) of iodine, 3.13 g (17.8 mmol) of periodic acid, 80 ml of aceticacid, 5 ml of sulfuric acid, 5 ml water and 2 ml chloroform were stirred at 65C for 3 h. After cooling, water was added to the mixture, and the precipitatedsolids were filtered off with suction, and washed three times with water. Thenthe product was recrystallized from dichloromethane / heptane. The yield is25.6 g (68 mmol), equivalent to 85% of theory.

The synthetic route of 50548-45-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Patent GMBH; Faram, Amir Hossain; Yatsi, Anya; Evemilley, Thomas; Grossman, Tobias; Krevor, Jonas Valentine; Tobelmann, Laruese; (100 pag.)KR2016/28524; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 69038-76-2, name is 4-Bromo-N1-methylbenzene-1,2-diamine, 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 69038-76-2, Computed Properties of C7H9BrN2

After methyl dichloro(methoxy)acetate (2.5 ml) was added to a solution of 4-bromo-N1-methylbenzene-1,2-diamine (1.0 g), N,N-diisopropylethylamine (7.1 ml) in 1,2-dichloroethane (30 ml), the reaction mixture was stirred at room temperature for 1 hour, and then stirred at 60 C. for 3 days. After the reaction mixture was cooled to room temperature, a saturated aqueous sodium hydrogen carbonate solution was added thereto, and extraction was carried out using chloroform. After the organic layer was dried over anhydrous sodium sulfate, the desiccant was removed, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate), thereby obtaining methyl 5-bromo-1-methyl-1H-benzimidazole-2-carboxylate (820 mg) as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-N1-methylbenzene-1,2-diamine, and friends who are interested can also refer to it.

Reference:
Patent; ASTELLAS PHARMA INC.; Ohnuki, Kei; Azami, Hidenori; Sawada, Yuki; Shin, Takashi; Kuramoto, Kazuyuki; Kikuchi, Shigetoshi; Saito, Tomoyuki; Hamaguchi, Hisao; Nagashima, Takeyuki; US2015/266869; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary