Month: September 2021

3638-73-1, name is 2,5-Dibromoaniline, 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. COA of Formula: C6H5Br2N

The 2,5-dibromo-aniline (3.74g, 14.9mmol), 4- methoxycarbonyl phenyl boronic acid (8.08g, 44.9mmol), palladium acetate (240mg, 1.07mmol) placed in 250mL round bottom flask, then added 40mLN , of N- dimethylformamide solvent, the addition of sodium carbonate (5.66g, 44.9mmol) was dissolved in 46mL of water dubbed aqueous sodium carbonate, aqueous sodium carbonate was added to the above 250mL round bottom flask. Then under nitrogen at a temperature of 60 , 18 hours. After the reaction was cooled to room temperature, suction filtered and washed with copious amounts of water. With ethyl acetate (100mL × 3) after the spin dry the solid solvent extraction, and finally washed with acetone to give the product as a gray solid.

The synthetic route of 3638-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wuhan University; Wang, Cheng; Meng, Xiangshi; Gui, Bo; (12 pag.)CN105503929; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 40422-70-6, name is 1-Bromo-3-(2-bromoethyl)benzene, A new synthetic method of this compound is introduced below., name: 1-Bromo-3-(2-bromoethyl)benzene

To a solution of 3-bromophenethylbromide (1 g, 3.83 mmol) in DMF (10 mL) was added 40% aqueous methylamine (2.97 mL, 38.3 mmol), followed by Cs2CO3 (1.625 g, 5 mmol). After the reaction mixture was refluxed for 1 h, it was cooled to room temperature and the solvent was removed. The residue was dissolved in ethyl acetate (30 mL), and the organic layer was washed with water (3 × 20 mL) and dried over Na2SO4. The solvent was removed in vacuo, and the oily residue was further purified using flash column chromatography (CHCl3/MeOH 5:2) yielding in 2 (100 mg, 12%) as a colorless liquid. 1H NMR (300 MHz, CDCl3): delta 7.26-7.23 (m, 2H, ArH), 7.06-7.04 (m, 2H, ArH), 2.78-2.74 (m, 4H), 2.30 (s, 3H, NCH3); TLC Rf: 0.2 (CHCl3/MeOH 5:2); GC-MS (EI) m/z (% rel Int.): 214 (100.0 [M]+), rt: 7.240 min (full analytical data are reported in27).

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:
Article; Herth, Matthias M.; Hansen, Hanne D.; Ettrup, Anders; Dyssegaard, Agnete; Lehel, Szabolcs; Kristensen, Jesper; Knudsen, Gitte M.; Bioorganic and Medicinal Chemistry; vol. 20; 14; (2012); p. 4574 – 4581;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1435-51-4, A common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, molecular formula is C6H3Br2F, 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.

General procedure: Palladium reagents were synthesized following the scheme of Figure 14 for generalprocedure A. In a nitrogen-filled glovebox, an oven-dried scintillation vial (1 0 mL), whichwas equipped with a magnetic stir bar and fitted with a Teflon screwcap septum, vascharged with RuPhos (2.5 equiv), a dihaloaryl compound (1 equiv) and cydohexane (1.2mL). Solid [(1,5-COD)Pd(CH2Si:Me3)] (2.5 equiv) was added rapidly in one portion and theresulting solution vvas stirred for 16 hat Jt. After this time, pentane (3 mL) was added andthe resulting mixture vas placed into a -20 C freezer for 3 h. The vial was then takenoutside of the glove box, and the resulting precipitate was filtered, washed with pentane (3 X3 mL), and dried under reduced pressure to afford the oxidative addition complex (Figure14)

The synthetic route of 1435-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; BUCHWALD, Stephen, L.; PENTELUTE, Bradley, L.; ZHANG, Chi; (170 pag.)WO2017/151910; (2017); A2;,
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. name: 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

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. 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, A new synthetic method of this compound is introduced below., name: 5-Bromo-N1-methylbenzene-1,2-diamine

To a round bottom flask was added 4-bromo-N2-methylbenzene-1,2-diamine (1-2) (9.07 g, 45.1 mmol), sulfamide (8.84 g, 92 mmol), and finally anhydrous pyridine (75 mL). The reaction mixture was then heated to 125C while stirring in a hot oil bath with a water cooled reflux condenser attached under an atmosphere of nitrogen for 14 hours. The crude reaction mixture was then allowed to cool to room temperature, suspended in ethyl acetate and added 6N HCl until pH <3. Crude mixture was then filtered. Filtrate organics were separated, then washed with 6N HCl twice dried over sodium sulfate, filtered, and concentrated to give 6- bromo-1 -methyl- 1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (1-3). HRMS (M+H)+:observed = 262.9486, calculated = 262.9484. The synthetic route of 337915-79-4 has been constantly updated, and we look forward to future research findings. Reference:
Patent; MERCK SHARP & DOHME CORP.; LAYTON, Mark, E.; KELLY, Michael, J.; HARTINGH, Timothy, J.; WO2011/109277; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route 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

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. 10269-01-9, name is (3-Bromophenyl)methanamine, A new synthetic method of this compound is introduced below., Formula: C7H8BrN

To a solution of commercially available 3-bromo-benzylamine (938 mg) in dry dichloromethane (10 mL) was added added di-tert-butyl dicarbonate (1.10 g). The resulting clear solution was stirred at room temperature for 15 h and then concentrated to afford the title compound (1.42 g; 99%). [(M-isobutene)H]+=230/232, [MNa]+=308/310.

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; Alantos Pharmaceuticals, Inc.,; US2006/173183; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

4263-52-9, A common compound: 4263-52-9, name is Sodium 2-bromoethanesulphonate, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Potassium O-ethylxanthate (3 x 95mg, O.deltaOmmol) is added portion wise every 1 .5 hours to a solution of sodium 2-bromoethanesulphonate (0.42g, 2.00mmol) in acetonitrile (15ml). The reaction mixture is heated at 850C, under a nitrogen atmosphere, for a total of 6 hours. Upon cooling the suspension is filtered, washed with acetonitrile and air-dried affording an off-white solid.1 H NMR (DMSO d6) delta (ppm) 4.67 (q, 2H), 3.40 (2H, m), 3.26 (m, 2H), 1 .39 (t, 3H).

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, Sodium 2-bromoethanesulphonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UCB PHARMA S.A.; WO2009/19119; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 112279-72-8, 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. 112279-72-8 name is 4-Bromo-2,3-difluoroaniline, 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.

N-((4-bromo-2,3-difluorophenyl)carbamothioyl)benzamide was prepared according to the following procedure. To 4-bromo-2,3-difluoroaniline (3.70 g, 17.8 mmol) dissolved in acetone (20 mL) was added benzoyl isothiocyanate (2.90 g, 2.39 mL, 1 eq, 17.8 mmol) drop-wise. The reaction was stirred for 30 min at 18 C, the mixture was filtered, the collected white solid was washed with heptane (50 mL) and vacuum dried to afford N-((4-bromo-2,3-difluorophenyl)carbamothioyl)benzamide (5.68 g, 85%) as a white solid.?H NMR (300 MHz, DMSO-ifc) d 12.45 (s, 1H), 11.91 (s, 1H), 8.46 – 7.88 (m, 2H), 7.78 – 7.26 (m, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,3-difluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; ACUCELA INC.; ORME, Mark, W.; ZUNIGA, Edison, S.; KUKSA, Vladimir, A.; CRAFT, Russell, Stuart; SAVEEDRA, Eduardo, Moreno; MEISSNER, Johannes, Wilhelm, Georg; DEN HARTOG, Jacobus, Antonius, Joseph; DROS, Albert, Cornelis; (223 pag.)WO2020/69330; (2020); A2;,
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. COA of Formula: C6H11Br

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