Month: September 2021

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. 4117-09-3, name is 7-Bromo-1-heptene, A new synthetic method of this compound is introduced below., COA of Formula: C7H13Br

9-Hept-6-enyloxy-5-hydroxymethyl-2-isopropyl-l-methyl-l,4,5,6-tetrahydro- 2H-benzo[e][l,4]diazoein-3-one (3): 7-Bromo-l-heptene (44 muL, 0.29 mmol), KI (72 mg, 0.43 mmol), and K2CO3 (80 mg, 0.58 mmol) were added to a solution of compound 2 (40 mg, 0.14 mmol) in anhydrous N,iV-dimethylformamide (DMF; 2 mL), and then heated at 8O0C for 8 h. The mixture was cooled and extracted with EtOAc (50 mL), washed with H2O (30 mL) and brine (30 mL), dried over anhydrous Na2Stheta4 (sodium sulfate), concentrated, and purified by column chromatography to afford compound 3 (17 mg, 31%); [af£ -221.23 (c=0.09 in MeOH); 1H NMR (400 MHz, CDCl3): delta=6.93 (brs, 1 H), 6.92 (d, /=8.0 Hz, 1 H), 6.52 (d, /=4.0 Hz, 1 H), 6.41 (dd, /=4.0, 8.0 Hz, 1 H), 5.87-5.77 (m, 1 H), 5.03-4.94 (m, 2 H), 3.93- 3.89 (m, 3 H), 3.72-3.66 (m, 2 H), 3.50-3.48 (m, 2 H), 3.03 (dd, /=8.0, 16.0 Hz, 1 H), 2.77 (s, 3 H), 2.77-2.69 (m, 1 H), 2.45-2.37 (m, 1 H), 2.09-2.08 (m, 2 H), 1.79- 1.76 (m, 2 H), 1.47- 1.46 (m, 4 H), 1.05 (d, /=8.0 Hz, 3H), 0.87 ppm (d, /=8.0 Hz, 3H); 13C NMR (100 MHz, CDCl3): delta =174.4, 159.0, 152.8, 139.0, 132.5, 123.2, 1 14.7, 106.8, 106.6, 70.0, 68.1, 66.1 , 54.8, 36.7, 35.3, 33.9, 29.4, 28.9, 28.5, 25.8, 20.7, 20.1 ppm; ESI-HRMS calculated for [C22H34N2O3+H]”: 375.2648, found: 375.2642; HPLC purity: 95.1 %.

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; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; KOZIKOWSKI, Alan; CHEN, Yihua; WO2010/17272; (2010); A2;,
Bromide – Wikipedia,
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Some common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-difluorobenzene, molecular formula is C6H3BrF2, 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. Product Details of 399-94-0

A solution of isopropylmagnesium chloride in THF (2M, 604 mL) was added dropwise to a solution of 2-bromo-1,4-difluorobenzene (244.7 g) in THF (1 L) that had been cooled to -50C. After completion of the dropwise addition, the temperature was warmed to 0C while stirring for 1 h. The reaction mixture was cooled to -50C again. To the reaction mixture was added a solution of 4-chloro-N-methoxy-N-methylbutyramide (100 g) in THF (200 mL) dropwise under stirring, and gradually warmed to 30C and then continuously stirred at 30C for 3h. The reaction mixture was quenched with a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The collected organic phase was washed with water and then a saturated saline solution. The organic layer was separated, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to afford the title compound (101 g). 1H NMR (400 MHz, CDCl3) delta 7.59-7.55 (m, 1H), 7.26-7.20 (m, 1H), 7.17-7.11 (m, 1H), 3.68-3.65 (m, 2H), 3.20-3.16 (m, 2H), 2.25-2.19 (m, 2H). m/z=219[M+1]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 399-94-0, its application will become more common.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; Centaurus BioPharma Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; ZHU, Li; HU, Yuandong; WU, Wei; DAI, Liguang; DUAN, Xiaowei; YANG, Yanqing; SUN, Yinghui; HAN, Yongxin; PENG, Yong; KONG, Fansheng; LUO, Hong; YANG, Ling; XU, Hongjiang; GUO, Meng; ZHONG, Zhaobai; WANG, Shanchun; (80 pag.)EP3533796; (2019); A1;,
Bromide – Wikipedia,
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These common heterocyclic compound, 52997-43-0, name is 7-(Bromomethyl)pentadecane, 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. Recommanded Product: 52997-43-0

General procedure: General procedure for the synthesis of a1-a6: To a solution of indoline-2,3-diones (10 mmol) in DMF (40 mL) was added K2CO3(15 mmol, 2.073 g) and 7-(bromomethyl)pentadecane (11 mmol,3.358 g) under nitrogen. The mixture was stirred at 70 C and monitoredby TLC. After the reaction completed, water was added, andextracted with EtOAc. The organic layer was combined and dried withMgSO4. After evaporation of the solvent, the residue was purified bycolumn chromatograph (eluent: Petroleum/EtOAc=20:1) to give thetarget compound.

The synthetic route of 7-(Bromomethyl)pentadecane has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hu, Qian; Jiang, Hua; Cui, Zhihua; Chen, Weiguo; Dyes and Pigments; vol. 173; (2020);,
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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. 69321-60-4, name is 2,6-Dibromotoluene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 69321-60-4

32.1) 2-(3-Bromo-2-methyl-phenyl)-pyridine (intermediate 101): A solution of i-PrMgCI (27.49 ml_, 2M in THF, 55 mmol.) was added dropwise to commercially available 1 ,3-dibromo-2-methyl-benzene ( 12.5 g, 50 mmol) at RT under argon and then heated at 65C for 1.5 h. The mixture was added via syringe to a suspension of dry ZnCb (6.83 g, 50 mmol.) in dry THF (20 ml) and cooled to 00C under argon. The resulting suspension was stirred at RT for 30 min. Then 2-bromo-pyridine (4.78 ml, 50 mmol.) and PdCI2*dppf (2.03 g) were added and the mixture was refluxed for 2 h. The reaction mixture was then quenched by the addition of a 5% solution of citric acid (200 ml) and extracted with ethyl acetate (2x 250ml). The combined organic layers were consecutively washed with a 5% solution of citric acid (150ml) and brine (150 ml), dried over Na2SO4, filtered and evaporated under reduced pressure. The crude material was chromatographed on silica gel. Yield: 7.7 g, 78 %.

The synthetic route of 69321-60-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; WO2009/103440; (2009); A1;,
Bromide – Wikipedia,
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22385-77-9, 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 22385-77-9 as follows.

To a solution of 1-bromo-3,5-di-tert-butylbenzene (527 mg, 1.96 mmol) in Et2O (10mL) at -78 C under N2 atmosphere was added dropwise n-BuLi (1.65 M in hexane, 1.1mL, 1.82 mmol). The resulting solution was warmed to room temperature and stirredfor 1 h. This solution was added dropwise to a solution of5,15-bis(triisopropylsilylethynyl)porphyrin2 (200 mg, 298 mumol) in dry THF (10 mL).After the mixture was stirred at room temperature overnight, water (1.0 mL) and thenDDQ (204 mg, 90.0 mumol) were added. The reaction mixture was stirred for additional 20 min before addition of triethylamine (0.2 mL). The volatiles were removed in vacuoand the residue was taken up in CH2Cl2 and washed with water and brine. The organiclayer was dried over Na2SO4 and concentrated. The residue was separated by silica-gelcolumn chromatography (CH2Cl2/hexane=1/4 as an eluent). After removal of thesolvent in vacuo, recrystallization from CH2Cl2/MeOH gave 5 (195 mg, 227 mumol) in76% yield as a purple solid. 1H NMR (400 MHz, CDCl3, RT): delta = 10.06 (s, 1H,meso-H), 9.72 (d, J = 4.4 Hz, 2H, beta-H), 9.64 (d, J = 4.8 Hz, 2H, beta-H), 8.87 (d, J = 4.8Hz, 2H, beta-H), 7.99 (d, J = 1.6 Hz, 2H, Ar-o), 7.81 (t, 2H, J = 1.8 Hz, Ar-p), 1.53 (s, 18H,tBu), 1.47 (s, 18H, tBu), 1.44 (s, 18H, tBu), and -2.40 (br, 2H, NH) ppm; 13C NMR(126 MHz, CDCl3): delta = 148.8, 140.7, 129.4 (br), 129.3, 123.7, 121.4, 106.2, 100.5,99.27, 35.0, 31.7, 19.1, 12.1, and 11.8 ppm; HR-MS (ESI): m/z = 859.5579 calcd for(C56H75N4Si2)+ = 859.5525 [(M+H)+].

According to the analysis of related databases, 1-Bromo-3,5-di-tert-butylbenzene, the application of this compound in the production field has become more and more popular.

Reference:
Article; Takiguchi, Asahi; Wakita, Mana; Hiroto, Satoru; Shinokubo, Hiroshi; Chemistry Letters; vol. 48; 4; (2019); p. 371 – 373;,
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Application of 2635-13-4,Some common heterocyclic compound, 2635-13-4, name is 5-Bromobenzo[d][1,3]dioxole, molecular formula is C7H5BrO2, 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 screw cap vial were added Pd(PPh3)2Cl2 (58.3 mg, 81.4 mumol), CuI (31.6 mg, 163 mumol),anhydrous DMF (0.33 mL), 4-bromo-1,2-(methylenedioxy)benzene (10d) (200 muL, 1.63 mmol)and Et3N (2.28 mL, 16.4 mmol) at rt. The solution was bubbled with argon gas for 5 min toremove the dissolved gases. Then, trimethylsilylethyne (350 muL, 2.44 mmol) was added, andthe reaction mixture was stirred at 90 C for 24 h. Upon completion of the reaction, the reaction mixture was concentrated by rotary evaporation. Purification by column chromatography(hexanes) yielded 11d (153 mg, 43%) as a brown liquid.

The synthetic route of 2635-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jeong, Yunkyung; Lee, Jooyeon; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry; vol. 24; 9; (2016); p. 2114 – 2124;,
Bromide – Wikipedia,
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Reference of 60956-23-2,Some common heterocyclic compound, 60956-23-2, name is 1,2-Dibromo-4-methylbenzene, molecular formula is C7H6Br2, 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.

General procedure: A 12 mL vial was charged with Pd(OAc)2 (2 mol%), BuPAd2 (6 mol%), and a stirring bar. Then, 2 ml dioxane and 1 mmol of bromobenzene were injected by syringe. The vial (or several vials) was placed in an alloy plate, which was transferred into a 300 mL autoclave of the 4560 series from Parr Instruments under argon atmosphere. After flushing the autoclave three times with NH3, a pressure of 2 bar NH3 and 2 bar CO was adjusted at ambient temperature. Then, the reaction was performed for 16 hours at 100 oC. After the reaction is finished, the autoclave was cooled down to room temperature and the pressure was released carefully. Then, CuI (5 mol%), DMEDA (10%), K2CO3 (3 mmol) and 1,2-dibromobenzene were added in under air, the vial was closed and heated to 110oC for 20 hours. The reaction mixture cooled down to room temperature. The solution was extracted 3-5 times with 2-3 ml of ethyl acetate from aqua solution. After evaporation of the organic solvent the residue was adsorbed on silica gel and the crude product was purified by column chromatography using n-heptane/AcOEt (20:1) as eluent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Dibromo-4-methylbenzene, its application will become more common.

Reference:
Article; Wu, Xiao-Feng; Neumann, Helfried; Neumann, Stephan; Beller, Matthias; Tetrahedron Letters; vol. 54; 24; (2013); p. 3040 – 3042;,
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Synthetic Route of 615-59-8,Some common heterocyclic compound, 615-59-8, name is 1,4-Dibromo-2-methylbenzene, molecular formula is C7H6Br2, 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 three-necked round-bottom flask equipped with a reflux condenser, thermometer, dropping funnel with pressure-equalizing, and magnetic stirring bar, and containing 74.9 g (0.30 mol) of 3,6-dibromotoluene, 15.5 ml (47.9 g, 0.30 mmol) of bromine was added dropwise under exposure to 500 W lamp for 3 hours at 19O0C. The resulting mixture was cooled to room temperature. Fractional distillation gave colorless liquid, b.p. 132-135°C/3 mm Hg. Yield 84.3 g (85percent).Anal. calc. for C7H5Br3: C, 25.57; H, 1.53. Found: C, 25.81; H, 1.62.1H NMR (CDCl3): delta 7.59 (m, IH, 5-H), 7.43 (m, IH, 3-H), 7.28 (m, IH, 3- H), 4.52 (s, 2H, CH2).13C NMR (CDCl3): delta 138.9, 134.6, 134.0, 133.1 , 123.0, 121.5, 32.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,4-Dibromo-2-methylbenzene, its application will become more common.

Reference:
Patent; EXXONMOBIL CHEMICAL PATENTS INC.; WO2007/70041; (2007); A1;,
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Related Products of 937046-98-5,Some common heterocyclic compound, 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, molecular formula is C6H5BrN4, 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 degassed solution of 7-bromopyrrolo[2,l-f][l,2,4]triazin-4-ylamine (10.0 g, 46.9 mmol) in anhydrous DMF (78 mL) and triethylamine (47 mL) was added tetrakis(triphenylphosphine)palladium(0) (2.17 g, 1.88 mmol, 0.04 eq) and copper (I) bromide dimethylsulfide complex (0.77 g, 3.75 mmol, 0.08 eq). After degassing with N2 for 5 min., propargyl alcohol (8.2 mL, 140.8 mmol, 3.0 eq) was added, and the reaction mixture was stirred at 900C for 6h. The reaction was quenched with 5% aq. NH3 in saturated aq. NH4Cl. The aqeuous layer was washed with EtOAc (Ix) followed by 25% iPrOH in DCM (3x). The combined organic layers were dried over MgSO4, filtered through a pad of celite, and concentrated at reduced pressure. The crude product was purified by MPLC eluted with 5% EtOH/DCM. Trituration from EtOAc afforded 4.75 g (53.8%) of the desired product as a yellow solid. 1H-NMR (DMSO-^6) §7.89 (s, IH), 7.88 (broad s, 2H), 6.85 (dd, 2H), 5.39 (t, IH), 4.36 (d, 2H); MS LC-MS [M+H]+ = 189, RT = 1.08 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-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, its application will become more common.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/64931; (2007); A2;,
Bromide – Wikipedia,
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875664-38-3, name is 1-Bromo-4,5-difluoro-2-methylbenzene, 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. Recommanded Product: 875664-38-3

Preparation 2 (4,5-Difluoro-2-methyl-phenyl)boronic acid n-Butyl lithium (4.6 mL, 11.5 mmol) is added to the mixture of 1-bromo-4,5-difluoro-2-methylbenzene (2.0 g, 9.6 mmol) and trimethyl borate (1.5 g, 14.5 mmol) in anhydrous tetrahydrofuran (30 mL), drop wise, at -78 C. over one hour, under an atmosphere of argon. The reaction mixture is stirred for another hour at the same temperature, quenched and acidified with 1 N HCl. The resulting mixture is extracted with ethyl acetate(3*). The combined organic layer is washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo.

The synthetic route of 875664-38-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; US2012/322841; (2012); A1;,
Bromide – Wikipedia,
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