Month: June 2021

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 64248-56-2 as follows. Recommanded Product: 2-Bromo-1,3-difluorobenzene

Preparation 105 Preparation of tert-Butyl 9-(2,6-difluorophenyl)-1,4,5,6-tetrahydroazepino-[4,5-b]indole-3(2H)-carboxylate. A solution of 1-bromo-2,6-difluorobenzene (0.28 g, 1.5 mmol) in dioxane (12 mL) was added to a flask charged with 3-(tert-butyloxycarbonyl)-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.50 g, 1.2 mmol), Pd2(dba)3 (0.11 g, 0.12 mmol) and potassium phosphate(0.59 g, 2.8 mmol). Next, trimethylphosphite (0.045 mL, 0.38 mmol) was added and the mixture was heated to 95 C. After 28.5 h, the reaction was cooled to rt, diluted with H2O, and extracted with EtOAc (3*50 mL). The combined organic extracts were washed with brine, dried over Na2SO4, decanted, and concentrated. The crude product was purified by column chromatography (Biotage, 40M, SIM) with heptane/EtOAc (4:1) to give 0.38 g (80%) of a pale yellow solid: mp 225.5-226 C.; % water (KF): 0.10; melt solvate: 1.46% CH2Cl2; 0.19% EtOAc; Anal. Calcd for C23H24F2N2O2-0.10% H2O·1.46% CH2Cl2·0.19% EtOAc: C, 68.34; H, 6.19; N, 6.91; found: C, 68.34; H, 6.19; N, 6.81.

According to the analysis of related databases, 64248-56-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Frank, Kristine E.; Acker, Brad A.; Ennis, Michael D.; Fisher, Jed F.; Fu, Jian-min; Jacobsen, Eric Jon; McWhorter JR., William W.; Morris, Jeanette K.; Rogier, Donald Joseph; US2002/77318; (2002); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 927384-44-9, 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 927384-44-9 as follows.

Bromo-1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-benzene 11 (2.40 g, 7.43 mmol), 4-(ethoxycarbonyl)phenylboronicacid 12 (2.40 g, 12.4 mmol), powdered tripotassium phosphate(3.40 g, 20.7 mmol) and 1,4-dioxane (150 cm3) were added to around-bottom flask fitted with a condenser and heated at 80 Cfor 15 min under N2. Pd(PPh3)4 (0.47 g, 0.41 mmol) was added tothe mixture which was purged with N2 for a further 15 min beforebeing stirred at 80 C for 2 days. The mixture was allowed to cool,filtered and the filtrate concentrated under reduced pressure. Theresulting residue was dissolved in chloroform (100 cm3), washedwith water (3 x 50 cm3) and brine (50 cm3) and concentratedunder reduced pressure to give a brown solid, which wasrecrystallised from chloroform and methanol to give 13 as largeyellow needles (yield 2.07 g, 71%). 1H NMR (CDCl3, 400 MHz) delta 8.25-8.04 (m, 2H), 7.85-7.67 (m, 6 H), 7.19 (dd, J = 7.3, 8.2 Hz,2H), 7.11 (d, J = 7.8 Hz, 2H), 6.48 (dd, J = 0.8, 7.3 Hz, 2H), 6.11 (s,2 H), 4.45 (q, J = 7.2 Hz, 2H), 1.46 (t, J = 7.2 Hz, 3H). ESI-TOF-MS:m/z 392.23 [M]+. Elemental Anal. Calc. for C25H21BN2O2: C, 76.55;H, 5.40; N, 7.14. Found: C, 76.51; H, 5.33; N, 7.26%. ATR-FTIR(cm-1): 3360 (s), 2900 (m), 1590 (s), 1580 (s), 1360 (m), 1260(s), 1080 (m), 756 (m, br), 728 (m).

According to the analysis of related databases, 927384-44-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Argent, Stephen P.; Tarassova, Irina; Greenaway, Alex; Nowell, Harriot; Barnett, Sarah A.; Warren, Mark R.; Tang, Chiu C.; Morris, Christopher G.; Lewis, William; Champness, Neil R.; Schroeder, Martin; Blake, Alexander J.; Polyhedron; vol. 120; (2016); p. 18 – 29;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 766-46-1, name is 2′-Bromophenylacetylene, 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 766-46-1, Product Details of 766-46-1

To a 10 mL screw cap vial, 2-bromophenylacetylene (0.5 mmol) and a solution of azidopentafluoroethane in THF (?0.60 mmol, 3-4 mL) were added. An aqueous solution of CuSO4-5H2O (1 mol·l-1, 0.05 mmol, 50 mul) and sodium L-ascorbate (1 mol·l-1, 0.05 mmol, 50 mul) were added, the vial was closed and the content was stirred at rt for 18 h. Saturated aqueous NH4Cl (10 mL) was added and the product was extracted into CH2Cl2 (3*10 mL). The combined organic phase was washed with water (2*10 mL), dried (MgSO4), filtered and solvent was removed under reduced pressure. Purification by column chromatography (silicagel) gave pure product as a white solid. Yield 37%; Rf (cyklohexane:EtOAc 95:5)=0.53; IR (CHCl3, film) v=1430, 1210, 1128, 1077, 972 cm; 1H NMR (400 MHz, CDCl3) delta=8.63 (s, 1H), 8.15 (dd, J=7.8, 1.7 Hz, 1H), 7.70 (dd, J=8.1, 1.2 Hz, 1H), 7.47 (td, J=7.6, 1.3 Hz, 1H), 7.29 (td, 1H); 13C NMR (101 MHz, CDCl3) delta=146.4, 133.9, 131.1, 130.6, 129.4, 128.1, 121.6, 121.4, 117.2 (qt, 1JC-F=287.5 Hz, 2JC-F=41.2 Hz, CF3), 110.3 (tq, 1JC-F=271.4 Hz, 1JC-F=43.2 Hz, CF2); 19F NMR (376 MHz, CDCl3) delta=-84.4 (s, 3F), -99.2 (s, 2F); HRMS (ESI) m/z calculated for C10H6N3BrF5 [M+H]+: 341.9660, found 341.9661.

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′-Bromophenylacetylene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ustav organicke chemie a biochemie AV CR, v.v.i.; CF Plus Chemicals s.r.o.; BEIER, Petr; MATOUSEK, Vaclav; BLASTIK, Zsofia E.; VOLTROVA, Svatava; (12 pag.)US2019/161452; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

67567-26-4, name is 4-Bromo-2,6-difluoroaniline, 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. Application In Synthesis of 4-Bromo-2,6-difluoroaniline

Example 1 5-Bromo-1,3-difluoro-2-nitro-benzene: To a suspension of sodium perborate tetrahydrate (1.04 g, 5 mmol) in acetic acid (20 m]L), stirred at 55 C., was added a solution of 4-bromo-2,6-difluoroaniline in acetic acid (10 mL) over 1 hour in a dropwise fashion. After stirring at 55 C. for an additional 3 hours, the solution was allowed to cool to room temperature and filtered. The filtrate was poured into ice, and extracted twice with ethyl acetate. The combined organic extracts were washed successively with 5*100-mL portions of water, brine, dried (MgSO4), and concentrated in vacuo. The resulting residue was purified by column chromatography over silica gel eluted with ethyl acetate:hexanes (1:20) to afford 780 mg of the titel compound as a tan solid. 1H NMR (CDCl3) delta 7.32 (dt, 2H).

The synthetic route of 67567-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Charifson, Paul S.; Deininger, David D.; Grillot, Anne-Laure; Liao, Yusheng; Ronkin, Steven M.; Stamos, Dean; Perola, Emanuele; Wang, Tiansheng; LeTiran, Arnaud; Drumm, Joseph; US2005/256136; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 2695-47-8, name is 6-Bromo-1-hexene, 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. SDS of cas: 2695-47-8

General procedure: Coupling of Alkyl Halides with t-BuMgCl; Procedure 1 (P1)An alkyl halide (1.0 mmol), decane (63 mg as an internal standard)and LiI (5.3 mg, 0.04 mmol) were added to a dry, nitrogen-flushedtest tube equipped with a rubber septum and a magnetic stir bar.THF (0.8 mL) was added and the solution was cooled to -78 C usinga dry ice/EtOH bath. t-BuMgCl (2a) (1.5 mL, 0.81 M in THF,1.2 mmol) was added slowly followed by isoprene (136.2 mg, 2.0mmol). To this mixture was added CoCl2 [2.6 mg, 0.02 mmol, as apowder or as a THF solution (0.5 mL, 0.04 M)]. (Note 1: CoCl2should be added after isoprene, otherwise the catalytic performancedecreases significantly). The cold bath was removed and the mixturewas warmed to r.t. (ca. over 10 min), and then heated for 5 h bysuspending the reaction vessel in an oil bath kept at 50 C. (Note 2:when the reaction mixture was heated at 30 C during this stage, unidentifiedside reactions occurred resulting in low yields of couplingproducts). The resulting mixture was cooled to 0 C in an ice bathand the reaction was quenched with aq HCl (5 mL, 1 M). The productwas extracted with Et2O (3 × 20 mL). The combined organiclayer dried over Na2SO4, concentrated and analyzed by gas chromatographyto determine the GC yield. The residue was purified by silicagel column chromatography or by GPC. According to P1, 6-bromohex-1-ene (4s) (163 mg, 1.0 mmol) and s-BuMgCl (2g) (0.76 M in THF, 1.2 mmol) were reacted under standardconditions. After aqueous work-up, purification by GPC (withCHCl3 as the eluent) afforded the title compound.Yield: 120 mg (85%); pale yellow oil.IR (Zn/Se-ATR, neat): 2961, 2927, 2857, 1641, 1463, 1378, 991,910 cm-1.1H NMR (400 MHz, CDCl3): delta = 0.77 (d, J = 6.4 Hz, 3 H), 0.78 (t,J = 7.4 Hz, 3 H), 1.01-1.07 (br m, 2 H), 1.22-1.29 (br m, 7 H), 1.97(m, 2 H), 4.88 (dt, J = 10.1, 1.4 Hz, 1 H), 4.92 (dd, J = 17.2, 1.4 Hz,1 H), 5.74 (ddt, J = 17.2, 10.1, 6.9 Hz, 1 H).13C NMR (100 MHz, CDCl3): delta = 11.4, 19.2, 26.6, 29.3, 29.5, 33.9,34.3, 36.4, 114.1, 139.2.MS (EI): m/z (%) = 140 (39) [M]+, 125 (8), 111 (19).HRMS (EI): m/z [M]+ calcd for C10H20: 140.1565; found: 140.1561.

The synthetic route of 6-Bromo-1-hexene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Iwasaki, Takanori; Takagawa, Hiroaki; Okamoto, Kanako; Singh, Surya Prakash; Kuniyasu, Hitoshi; Kambe, Nobuaki; Synthesis; vol. 46; 12; (2014); p. 1583 – 1592;,
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. 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C7H3BrF4

To a solution of 4-bromo-3-fluoro-benzotrifluoride (585 mg, 2.36 mmol) in 15 mL of THF, stirred at -75 C. under nitrogen atmosphere, 1.53 mL (2.6 mmol) of a 1.7M solution of tert-butyllithium in pentane were added dropwise. The reaction mixture was stirred at -60 C. for 15 minutes then a solution of 2-methyl-propane-2-sulfinic acid-(tetrahydro-pyran-4-ylidene)-amide (400 mg, 1.97 mmol; prepared as described in literature: WO2005/87751 A2) in 10 mL of THF was added dropwise. The reaction mixture was allowed to reach room temperature and stirred for 1 hr. A saturated ammonium chloride solution was added and the reaction mixtures was extracted with ethyl acetate. The organic phases were collected, dried over sodium sulfate and concentrated under vacuum. The crude obtained was purified by flash chromatography (eluent: cyclohexane/AcOEt; gradient from 12% to 100% of AcOEt). The oil obtained was diluted in 2 mL of 1,4-dioxane, 0.4 mL of a 4 M solution of hydrochloric acid in 1,4-dioxane were added, the reaction mixture was stirred at room temperature for 1 hr and then concentrated under vacuum to obtain 100 mg of the title compound as white solid.LC-MS (Method 2): Rt=0.90 minMS (ESI pos): m/z=264 (M+H)+

The synthetic route of 40161-54-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; HOENKE, Christoph; BERTANI, Barbara; FERRARA, Marco; FOSSATI, Giacomo; FRATTINI, Sara; GIOVANNINI, Riccardo; HOBSON, Scott; (88 pag.)US2017/101411; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 3344-70-5, These common heterocyclic compound, 3344-70-5, name is 1,12-Dibromododecane, 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.

1.0 g of compound 3,2.63 g of 1,12-dibromododecane,0.43 g of potassium hydroxide and 0.16 g of tetrabutylammonium bromide,Was added to a mixture of 10 ml of dichloromethane and 6.5 ml of water,The mixture was stirred at room temperature under nitrogen for 24 hours,Washed twice with 30 ml of water,Washed once with 15 ml of saturated brine,The organic layer was separated,After adding anhydrous sodium sulfate to remove water,The solvent was removed on a rotary evaporator,(200: 300 mesh silica gel column chromatography elution (ethyl acetate / petroleum ether volume ratio of l: 30-l: 10),To give 1.19 g of the compound 4 as a pale yellow liquid,Yield 90percent.

Statistics shows that 1,12-Dibromododecane is playing an increasingly important role. we look forward to future research findings about 3344-70-5.

Reference:
Patent; Guilin University of Technology; Kong, Xiangfei; Dai, Shengping; Chang, Xiao; Zhang, Laiqi; Wang, Guixia; (10 pag.)CN106117220; (2016); A;,
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. Safety of 2,8-Dibromodibenzo[b,d]furan

1b) 2,8-Bis-((E)-styryl)-dibenzofuran Tetrethylamine hydroxide (13.6 g, 18.4 mmol), tetrakis(triphenylphosphine)palladium(0) (142 mg) and trans-2-phenylvinylboronic acid (2.3 g, 15.3 mmol) are added to a solution of the product from example 1a) (2.00 g, 6.14 mmol) in N,N’-Dimethylacetamide (DMA) (30 ml). The mixture is then stirred at 110 C. for 24 hours. The reaction mixture is cooled to room temperature and poured into H2O. A gray crude product is obtained after filtration and washing with n-hexane. The crude product is purified by silicagel column chromatography with CH2Cl2, which result in a white solid (71% yield, mp.: 226 C.). 1H-NMR (CDCl3, ppm): 7.26-7.30 (m, 6H), 7.39 (t, 4H), 7.54-7.58 (m, 6H), 7.65 (dd, 2H), 8.12 (d, 2H)

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

Reference:
Patent; Tanabe, Junichi; Oka, Hidetaka; Yamamoto, Hiroshi; US2009/131673; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 65185-58-2,Some common heterocyclic compound, 65185-58-2, name is 2-Bromophenethylamine, molecular formula is C8H10BrN, 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.

10.1.2: Methyl[2-(2-bromophenyl)ethyl]carbamate 5 g of 2-(2-bromophenyl)ethanamine and 10 g of potassium carbonate in 30 cm3 of anhydrous tetrahydrofuran are stirred under an inert atmosphere at a temperature close to 10 C. 2.5 cm3 of methyl chlorocarbonate in solution in 10 cm3 of tetrahydrofuran are poured into the reaction mixture. After returning to a temperature close to 20 C., the reaction mixture is heated for 2 h at the reflux of the solvent. The potassium carbonate is filtered and washed with tetrahydrofuran. The filtrate is concentrated using a rotary evaporator under reduced pressure (5 kPa). 3.43 g of methyl[2-(2-bromophenyl)ethyl]carbamate are obtained in the form of a colorless thick oil NMR: 2.85 (t, J=6.5 Hz, 2H); 3.22 (q, J=6.5 Hz, 2H); 3.51 (s, 3H); 7.18 (m, 1H); 7.22 (broad t, J=6.5 Hz, 1H); 7.31 (m, 2H); 7.59 (d, J=8.0 Hz, 1H)

The synthetic route of 65185-58-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; US2010/197725; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 7745-91-7, 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. 7745-91-7 name is 3-Bromo-4-methylaniline, 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.

Example 46A N-(3-Bromo-4-methylphenyl)-3-tert-butylbenzamide 285 mg (1.53 mmol) of 3-bromo-4-methylaniline, 300 mg (1.68 mmol) of 3-tert-butylbenzoic acid and 698 mg (1.83 mmol) of HATU were dissolved in 3 ml of DMF, 0.32 ml (1.83 mmol) of N,N-diisopropylethylamine were added and the mixture was stirred at RT for 16 h. The reaction was then stirred into 20 ml of 0.1 M aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic phase was washed with water and saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated under reduced pressure. Drying of the residue gave 490 mg (88% of theory) of the title compound. 1H NMR (400 MHz, DMSO-d6, delta/ppm): 10.26 (s, 1H), 8.10 (d, 1H), 7.76 (d, 1H), 7.67 (dd, 1H), 7.63 (d, 1H), 7.46 (t, 1H), 7.33 (d, 1H), 2.33 (s, 3H), 1.34 (s, 9H). LC/MS (Method 3, ESIpos): Rt=1.35 min, m/z=347 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-4-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; SUessMEIER, Frank; LOBELL, Mario; GRUeNEWALD, Sylvia; HAeRTER, Michael; BUCHMANN, Bernd; TELSER, Joachim; JOeRIssEN, Hannah; HEROULT, Melanie; KAHNERT, Antje; LUSTIG, Klemens; LINDNER, Niels; US2013/190290; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary