Tag: M.W=200-300

Synthetic Route of 22385-77-9,Some common heterocyclic compound, 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, molecular formula is C14H21Br, 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.

2,6-Bis(aniline)pyridine (500 mg, 1.914 mmol), 3,5-di-t-butyl-bromobenzene (1.26 g, 4.688 mmol), Pd2(dba)3 (87.6 mg, 95.7 mumol), BINAP (128.7 mg, 229.5 mumol) and sodium t-butoxide (552 mg, 5.744 mmol) were dissolved in 15 mL of toluene. The mixture was stirred for 48 h at 90 0C before cooling it to room temperature and quenching the reaction with 20 mL of water. After separation with dichloromethane, the volatiles were removed in vacuo from the organic extract. The obtained orange oil was passed through a silica gel column by a 20:1 mixture of dichloromethane and ethyl acetate and then was triturated from cold methanol and collected by filtration. 854 mg of pale-yellow solid 6a were obtained after a single wash (70 percent yield). 1H NMR (CDCl3) delta: 1.22 (s, 36eta, C(CH3)3), 6.93 (td, 2eta), 6.99 (t, 2H tBu-Ph-H), 7.05 (d, 4eta, tBu-Ph-H), 7.30 (td, 2eta), 7.54 (dd, 2H), 7.66 (d, 4H, Ph-H, Py-H), 7.90 (t, 1eta, Py-H), 9.8 (s, 2eta,NH). 1H-NMR (C6D6) delta: 1.22 (s, 36H, C(CH3)3), 6.86 (td, 2eta, Ph-H), 7.14 (t, 2eta), 7.1-7.2 (d+t, 3H, Py-H), 7.24 (td, 2eta, Ph-H), 7.32 (d, 4eta), 7.52 (dd, 2H, Ph-H), 7.85 (dd, 2eta, Ph-H), 10.14 (s, 2eta,NH). 13C NMR (CDCl3) delta: 31.6 (CH3), 35.0 (C(CH3)3), 114.6, 115.8, 116.1, 118.9, 120.5, 124.7, 130.0, 130.5, 138.5, 141.5, 143.2, 151.9, 157.3.

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-3,5-di-tert-butylbenzene, its application will become more common.

Reference:
Patent; CALIFORNIA INSTITUTE OF TECHNOLOGY; AGAPIE, Theodor; GOLISZ, Suzanne; TOFAN, Daniel; BERCAW, John, E.; WO2008/36882; (2008); A1;,
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61613-22-7, name is 2-Bromo-N-phenylaniline, 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. Formula: C12H10BrN

After dissolving 10 g of 2-bromo-N-phenylphenylamine in 100 ml of tetrahydrofuran, the reaction temperature was lowered to -78 C,Slowly add 20 ml of 2.5 M butyllithium and stir for 1 h. 11 g of benzophenone was dissolved in 100 ml of tetrahydrofuran and slowlyAfter dropping, the temperature was increased to room temperature and stirred for 12 h. After the reaction has ended, distilled water and methylene chloride will be usedRow extraction and drying by anhydrous magnesium sulfate followed by filtration under reduced pressure gave the solid which was dissolved in 100 ml of acetic acid, 7 ml of sulfuric acid was added dropwise and the mixture was reflux-stirred. After the reaction was completed, the mixture was extracted with distilled water and methylene chlorideThe resulting solid was purified by column chromatography to give Intermediate B-1 (7.1 g, yield 53%).

The synthetic route of 61613-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Liu Xiqing; Cai Hui; (24 pag.)CN107400085; (2017); A;,
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Application of 176317-02-5, A common heterocyclic compound, 176317-02-5, name is 1-Bromo-2,3,4-trifluorobenzene, molecular formula is C6H2BrF3, 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.

Step 1: 5-bromo-2,3,4-trifluorobenzoic acid To a solution of 1-bromo-2,3,4-trifluorobenzene (13.64 g, 64.6 mmol) in THF (120 mL) was added lithium diisopropylamide (2.0 M in THF, 33.9 mL, 67.8 mmol) at -78 C. under nitrogen atmosphere. 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 (300 mL) and extracted with ethyl acetate (200 mL*3). The combined organic extracts were washed with 5% sodium hydroxide (300 mL). The aqueous layer was acidized to pH 1 and extracted with ethyl acetate (200 mL*3). The combined organic extract was dried over Na2SO4, filtered and concentrated under reduced pressure to afford the desired product (white solid, 13.51 g, 82% yield). 1H NMR (400 MHz, CDCl3): delta 13.94 (s, 1H), 7.95 (m, 1H).

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

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

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. Recommanded Product: 4-Bromo-3,3,4,4-tetrafluorobut-1-ene

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;,
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