Tag: M.W=100-200

Reference of 53078-85-6,Some common heterocyclic compound, 53078-85-6, name is 2-Bromo-5-methylaniline, molecular formula is C7H8BrN, 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.

8-bromo-4,5-dimethylquinoline, monohydrochloride (A): At 23 C, a 2-neck500 mL round-bottom flask equipped with magnetic stuffing bar, reflux condenser, and bubbler was flushed with N2 for several minutes. The flask was placed in a bath ofaluminum beads and charged with 12 N aq. HC1 (180 mL). Molten 2-bromo-5-methyl benzenamine (50.0 g, 0.270 mol) was added steadily to the flask while the aluminum bead bath was at 23 C. Once addition ensued, an off-white chunky precipitate formed. A glass stirring rod was periodically used to pulverize the chunks. Once addition was complete, the reaction was a suspension with particulate white solid in yellow liquid.At this point, a pressure-equalizing addition funnel was attached to the flask and charged with Methyl Vinyl Ketone (26.8 mL, 0.322 mol). The reaction was heated to 120 C under N2. A circulating chiller was applied to through the reflux condenser. The bubbler was then removed and a stream of air was passed steadily over the reaction while the Methyl Vinyl Ketone was added dropwise over 10 mm. Heating wascontinued for another 30 mm, then the air stream was cut. The reaction was refitted with the bubbler and an N2 stream was applied as the reaction was cooled to 23 C. The reaction was poured into THF (1.0 L) and the sluffy was cooled to – 20 C overnight. The precipitate was collected in a Buchner funnel on filter paper and washed with 2 x 100 mL of ice-cold THF. This afforded 8-bromo-4,5-dimethylquinoline,monohydrochioride. The material was immediately used in the reaction below. LCMSESI Calc?d for C11H10BrN (M+H): 236.0 / 238.0. Found 236.1 / 238.1 (M+H)

The synthetic route of 53078-85-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; BABAOGLU, Kerim; MCFADDEN, Ryan; MITCHELL, Michael, L.; WO2015/179448; (2015); A1;,
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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;,
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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;,
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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;,
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Related Products of 583-75-5, 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. 583-75-5, name is 4-Bromo-2-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

6-bromo-8-methylquinoline. Glycerol (2.3 ml, 32.2 mmol) was added dropwise via syringe to a solution of 4-bromo-2-methylaniline (5.00 g, 26.8 mmol) and sodium iodide (52 mg, 0.349 mmol) in 75% aq H2SO4 (15.81 ml, 120 mmol) at 140 C. The mixture was held at this temperature for 3 hours. The reaction mixture was neutralized to a pH of 7 with aq NaOH. This mixture was extracted with EtOAc and the combined organics were washed with brine, dried over MgSO4 and concentrated. Column chromatography on silica gel (5-25% EtOAc in hexanes) afforded intermediate 11 (5.50 g, 24.7 mmol, 92%). 1H NMR (400 MHz, CDCl3) delta ppm 8.93 (dd, J=4.28, 1.76 Hz, 1H), 8.03 (dd, J=8.31, 1.76 Hz, 1H), 7.82 (d, J=2.01 Hz, 1H), 7.65 (d, J=1.01 Hz, 1H), 7.40 (dd, J=8.18, 4.15 Hz, 1H), 2.78 (s, 3H). Mass 221 [M+H]+.

The synthetic route of 4-Bromo-2-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/18163; (2009); 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. 7051-34-5, name is (Bromomethyl)cyclopropane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C4H7Br

a) 3-cyclopropylmethoxy-4-difluoromethoxy-benzaldehyde 4.70 g (24.98 mmol) 4-difluoromethoxy-3-hydroxybenzaldehyde are placed in 50 ml of dimethylformamide, 4.00 g (29.63 mmol) bromomethylcyclopropane and 3.50 g (25.32 mmol) potassium carbonate are added. The reaction mixture is heated to 100 C. for 20 hours, then the dimethylformamide is concentrated by evaporation. The residue is extracted with ethyl acetate and water, the organic phase is dried and evaporated to dryness. Yield: 5.83 g (96% of theoretical)

The synthetic route of 7051-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2006/116373; (2006); A1;,
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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. 399-94-0, name is 1-Bromo-2,5-difluorobenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H3BrF2

2.0 M Isopropyl magnesium chloride solution in THF (163mL, 324.3 mmol) was added to a solution of 2-bromo-l,4-difluorobenzene (62.5 g, 324.3 mmol) in THF (350mL) at -40C and stirring was continued at 5C for 1 h. tert- utyl 2- oxopyrrolidine-l-carboxylate(Step-l)(73 g, 392 mmol) in THF(150mL) was added dropwise to above reaction mixture at -40C and stirring was continued at 10C for 2 h. Reaction mixture was quenched with saturated NH4CI solution, extracted with EtOAc, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 76 g of the title compound.

The synthetic route of 399-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; SASMAL, Pradip Kumar; AHMED, Shahadat; TEHIM, Ashok; PRADKAR, Vidyadhar; DATTATREYA, Prasanna M.; MAVINAHALLI, Nanjegowda Jagadeesh; WO2013/88256; (2013); A1;,
Bromide – Wikipedia,
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Some common heterocyclic compound, 108-85-0, name is Bromocyclohexane, molecular formula is C6H11Br, 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

EXAMPLE 7; Entry No. 7-1 to Entry No. 7-6 Following the details given below, effects of various metallic reagents and halides on yield of the products were examined. A mixture of various aromatic zinc reagents shown by ArZnX (X = Br, I) (0.5 M THF solution, 4.0 mL, 2.0 mmol) and magnesium compounds shown by Me3SiCH2MgCl (1.1 M Et2O solution 1.8 mL, 2.0 mmol) was charged in a dry reactor and stirred at 0C for 0.5-1 hour. To the solution obtained, TMEDA (0.30 mL, 2.0 mmol), various halides (shown by “(FG)Ralkyl-X” in TABLE 6) (1.0 mmol) and then FeCl3 (0.1 M THF solution, 0.5 mL, 0.05 mmol) were added at 0C. The reaction mixture was stirred at 30C for 6 hours. Saturated NH4Cl aqueous solution was added to terminate the reaction. The mixture was filtered through a pad of Florisil (registered trademark) and concentrated in vacuum. The residue was purified by silica gel chromatography Entry No. 7-4 (4-Cyclohexylbenzonitrile) Halide: 3-bromocyclohexane (1.0 mmol) Aromatic zinc reagent: 4-cyanophenylzinc bromide (2.0 mmol) Reaction time: 6 hours Colorless oily substance (167 mg, 90%) FTIR (neat): cm-1 2925 (s), 2852 (m), 2227 (m), 1607 (m), 1505 (m), 1449 (m), 1415 (w), 1177 (w), 1000 (w), 823 (s); 1H NMR (500 MHz, CDCl3): delta 7.56 (d, J = 8.6 Hz, 2H), 7.30 (d, J = 8.6 Hz, 2H), 2.12-2.00 (m, 1H), 1.92-1.80 (m, 4H), 1.80-1.69 (m, 1H), 1.47-1.33 (m, 4H), 1.33-1.20 (m, 1H); 13C NMR (125 MHz, CDCl3): delta 153.4, 132.1 (2C), 127.6 (2C), 119.1, 109.5, 44.7, 33.9 (2C), 26.6 (2C), 25.9; Elemental analysis: Calcd. for C13H15N: C, 84.28; H, 8.16; N, 7.56. Found: C, 84.12; H, 8.36; N, 7.36.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 108-85-0, its application will become more common.

Reference:
Patent; Japan Science and Technology Agency; EP1724248; (2006); A1;,
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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. 2924-09-6, name is 5-Bromo-2-fluoroaniline, A new synthetic method of this compound is introduced below., COA of Formula: C6H5BrFN

98% of 2-fluoro-5-bromonitrobenzene (211 g, 0.96 mol) and iron powder (212 g, 3.8 mol) were mixed, 1200 ml of ethanol was added and glacial acetic acid (456 g, 7.6 mol) was added dropwise at room temperature. The reaction solution was treated with an oil bath at 60 CThe reaction solution was completed by a gas phase controlled reaction. The reaction solution was filtered through a Buchner funnel pad and the filtrate was evaporated to dryness and extracted with ethyl acetateN-heptane (volume ratio 1: 4) was purified by column and evaporated to give pure product 122.5 g, 98% GC, yield 62.5%

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; Dalian Allychem Co., Ltd.; Wang, Xianxue; Zheng, Peng; (5 pag.)CN104530107; (2016); B;,
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Adding a certain compound to certain chemical reactions, such as: 656-64-4, name is 3-Bromo-4-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 656-64-4, name: 3-Bromo-4-fluoroaniline

3-bromo-4-fluoroaniline (415mg, 2.18mmol), cyclopropylboronic acid (244mg, 2.84mmol), Pd (OAc) 2 (25mg, 0.11mmol), tricyclohexylphosphine (61mg, 0.22mmol), Potassium phosphate (1.62g, 7.64mmol) was dissolved in toluene (12mL) and water (1mL), protected by argon, and reacted at 100 C for 16h. The raw materials disappeared. Cool to room temperature, add EA (20 mL), wash with saturated brine (20 mL × 2), wash with water (20 mL × 2), and column chromatography (P / E = 10: 1) to obtain 235 mg of brown oil, yield 71.2% .

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, 3-Bromo-4-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xu Boling; Chen Xiaoguang; Cui Guonan; Lai Fangfang; Zhou Jie; Ji Ming; Wang Xiaoyu; Du Tingting; Li Ling; Jin Jing; (144 pag.)CN110483366; (2019); A;,
Bromide – Wikipedia,
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