Month: September 2021

Reference 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 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

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. category: bromides-buliding-blocks

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

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. 69902-83-6, name is 1-Bromo-2-methyl-3-(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Bromo-2-methyl-3-(trifluoromethyl)benzene

Bromo-3- (trifluoromethyl) -2-methylbenzene (5.0 g, 20.9 mmol),Bromosuccinimide (3.72 g, 20.9 mmol),Azobisisobutyronitrile (300 mg) was dissolved in dry carbon tetrachloride (100 mL)Heat under reflux for 16 hours under nitrogen.The reaction was cooled to room temperature and filtered,The filtrate was added imidazole (2.85 g, 42 mmol) and potassium carbonate (4.34 g, 31.37 mmol)Heat under reflux for 5 hours under nitrogen.LC-MS showed the reaction was complete,The reaction solution was filtered,The filtrate was concentrated,The residue was dissolved in dichloromethane (50 mL)Wash with water (2 × 40 mL).Organic phase filtration,concentrate,The residue was purified by flash silica gel column to give 1- (2-bromo-6- (trifluoromethyl) benzyl) -1H-imidazole (5.0 g).

According to the analysis of related databases, 69902-83-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Jiangsu Haosen Pharmaceutical Group Co., Ltd.; Tong Chaolong; Bao Rudi; Li Yuannian; (67 pag.)CN107312005; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

393-36-2, These common heterocyclic compound, 393-36-2, name is 4-Bromo-3-(trifluoromethyl)aniline, 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.

4-Bromo-3-(trifluoromethyl)aniline was converted into 4-bromo-3-(trifluoromethyl)phenyl isocyanate according to Method B1. According to Method C1a, 4-bromo-3-(trifluoromethyl)phenyl isocyanate was reacted with 4-(2-(N,N-dimethylcarbamoyl)-4-pyridyloxy)aniline to afford the urea. Entry 92: 4-Chloro-N-methylpyridinecarboxamide was synthesised as described in Method A2, Step 3b.

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 393-36-2.

Reference:
Patent; Riedl, Bernd; Dumas, Jacques; Khire, Uday; Lowinger, Timothy B.; Scott, William J.; Smith, Roger A.; Wood, Jill E.; Monahan, Mary-Katherine; Natero, Reina; Renick, Joel; Sibley, Robert N.; US2001/11135; (2001); A1;; ; Patent; BAYER CORPORATION; US2003/181442; (2003); 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. category: bromides-buliding-blocks

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

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. 73918-56-6 name is 2-(4-Bromophenyl)ethanamine, 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. 73918-56-6

General procedure: To a solution of neocrotocembraneic acid (150 mg, 0.50 mmol) in dry CH2Cl2 (10 mL) were added HOBt (81 mg, 0.60 mmol) and EDCI (115 mg, 0.60 mmol). The mixture was stirred at room temperature for 2 h, and then the corresponding amines (0.6 mmol 1.2 equiv.) were added. Upon completion, the reaction mixture was washed successively with 1M hydrochloric acid, saturated NaHCO3 and brine, then dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography to give the amide derivatives 8a-8r.

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

Reference:
Article; Shang, Hai; Li, Ling-Yu; Cheng, Wei-Hua; Luo, Jun; Zhang, Hong-Wu; Zou, Zhong-Mei; Molecules; vol. 21; 11; (2016);,
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. 176317-02-5, name is 1-Bromo-2,3,4-trifluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H2BrF3

Step 1: 5-bromo-2,3,4-trifluorobenzoic acid To a solution of diisopropylamine (10.14 g, 100.20 mmol) in THF (100 mL) was added n-BuLi (40.08 mL, 2.5 M in hexane, 100.20 mmol) at -78 C. under nitrogen atmosphere. The stirring was maintained at this temperature for 1 h. Then a solution of 1-bromo-2,3,4-trifluorobenzene (17.62 g, 83.50 mmol) in THF (120 mL) was added. After stirring for 1 h at -78 C., the mixture was transferred to a bottle with dry ice. The mixture was stirred overnight at room temperature. The reaction was quenched with 10% aqueous HCl and pH was adjusted to 1-2. The mixture was extracted with ethyl acetate (100 mL*3). The combined organic extracts were washed with water (100 mL) and brine (100 mL) sequentially, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the desired product (20.12 g, 94.5% yield). 1H NMR (400 MHz, DMSO-d6): delta 13.95 (s, 1H), 7.97 (m, 1H).

According to the analysis of related databases, 176317-02-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TIANJIN BINJIANG PHARMA, INC.; Tian, Hongqi; Ji, Conghui; Liu, Chunlei; Kong, Li; Cheng, Ying; Huang, Gongchao; US2014/371278; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature 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

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. 18599-22-9, name is 4-Bromo-3,3,4,4-tetrafluorobut-1-ene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 18599-22-9

In a two-necked round-bottomed flask, equipped with a teflon-coated stirrer bar, were placed 4-nitrobenzoyl chloride (5g, 0.50 g 2.7 mmol), Cu2O (0.030 g, 0.21 mmol), 2,2′-bipyridyl (0.020 g, S29 0.13 mmol), and a DMF solution of 2-Zn (0.66 M, 1.0 mL, 0.66 mmol), and the whole were stirred at 100 C for 20 h. The resultant was poured into water and the organic products were extracted with Et2O three times. The combined organic layers were dried over anhydrous Na2SO4, then filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to give the corresponding 6g (0.14 g, 0.51 mmol) in 77% yield as a pale yellow oil.2,2,3,3-Tetrafluoro-1-(4-nitrophenyl)pent-4-en-1-one (6g) Yield: 77% (0.14 g, 0.51 mmol); Pale yellow oil (hexanes/AcOEt = 5/1, Rf = 0.50); 1H NMR (CDCl3): delta 5.78 (d, J = 11.0 Hz, 1H, cis-CH2=CH), 5.91 (dt, J = 17.31, 1.68 Hz, 1H, trans-CH2=CH), 6.07 (dtd, J = 17.3, 11.9, 11.0 Hz, 1H, CH2=CH), 8.21 (d, J = 8.4 Hz, 2H, Ar-H), 8.30-8.33 (m, 2H, Ar-H); 13C NMR (CDCl3): 111.7 (tt, J = 264.9, 37.4 Hz, CF2), 114.7 (tt, J = 250.6, 31.4 Hz, CF2), 123.9 (Ar), 125.6 (t, J = 23.9 Hz, CH2=CH), 125.6 (t, J = 9.4 Hz, CH2=), 131.4 (t, J = 3.4 Hz, Ar), 136.7 (Ar), 151.2 (Ar), 185.1 (t, J = 28.0 Hz, C=O); 19F NMR (CDCl3): -115.04 (s, 2F, CF2-C=O), -113.37 (d, J = 11.9 Hz, 2F, =CH-CF2); IR (neat): 3057, 1715, 1604, 1531, 1351, 1156, 1014, 834 cm-1 ; HRMS (FAB) calcd for C11H8F4NO3 [M+H]+ : 278.0440, found 278.0435.

The synthetic route of 18599-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tamamoto, Ken; Yamada, Shigeyuki; Konno, Tsutomu; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 2375 – 2383;,
Bromide – Wikipedia,
bromide – Wiktionary