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

To a 100 mL three neck round bottomed flask under nitrogen atmosphere, (R)-2- isopropyl-3,6-dimethoxy -2,5- dihydropyrazine (4 g, 21.7 mmol) was dissolved in dry THF (28 mL) and cooled to -78 C. To this reaction mixture, 1.6 M solution of n-BuLi in hexanes (16.28 mL, 26 mmol) was added dropwise at -78 C and stirred at same temperature for 15 minutes. After 15 minutes, l-bromo-3- (2-bromoethyl)benzene (5.73 g, 21.7 mmol) in dry THF (13 mL) was added dropwise at -78 C and stirred at -78 C for 1 h followed by stirring at room temperature (rt) for 3 h. The reaction was monitored by TLC using ethyl acctatc hcxancs (0.3:9.7) as a mobile phase. After completion of the reaction, reaction mixture was quenched with saturated ammonium chloride solution (75 mL) and extracted using ethyl acetate (3 x 100 mL). Combined organic layer was dried over sodium sulphate and concentrated to give crude which was purified by flash column purification with 1-3 % ethyl acetate in hexanes to yield 3.3 g of (2S,5R)-2-(3-bromophenethyl)-5- isopropyl-3, 6-dimethoxy-2,5-dihydropyrazine (41.38% yield).

The synthetic route of 40422-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; LOU, Yan; OWENS, Timothy Duncan; BRAMELD, Kenneth Albert; GOLDSTEIN, David Michael; (171 pag.)WO2019/99576; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 629-03-8, The chemical industry reduces the impact on the environment during synthesis 629-03-8, name is 1,6-Dibromohexane, I believe this compound will play a more active role in future production and life.

Preparation of 6-Bromohex-1-ene 1,6-Dibromohexane (30 mL, 48 g) was placed in a PTFE reactor vessel along with a magnetic stirrer bar. The reactor was set up with a 3 mm O.D. outlet tube connected to the cover assembly. The dibromide was heated to 150 C. and hexamethylphosphorous triamide (HMPTA; ca. 3 mL) was added through a second tube attached to the cover assembly, by means of a syringe. The vessel contents were then heated to 200 C. and HMPTA (42 mL) was added dropwise through the syringe. The crude product distilled through the exit tube and was collected in chilled flasks, then redistilled to give 6-bromohex-1-ene (15.6 g, 49%). 1 H NMR (CDCl3; 200 MHz): delta1.56, m, 2H, CH2; 1.85, m, 2H, CH2; 2.10, m, 2H, CH2; 3.41, t, J=7 Hz, 2H, CH2 Br; 4.85-5.10, m, 2H, =CH2; 5.80, m, 1H, =CH, in agreement with that reported by Kenneth J.

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, 1,6-Dibromohexane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Commonwealth Scientific and Industrial Research Organisation; US5932075; (1999); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 105309-59-9, 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. 105309-59-9 name is Tetrakis(4-bromophenyl)methane, 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.

To a solution of tetrakis(4-bromophenyl)methane (0.6360 g,1 mmol) and N-(tert-butoxycarbonyl)-pyrrol-2-ylboronic acid(1.0128 g, 4.8 mmol) in 30 mL of THF was added 10 mL of a saturatedaqueous solution of potassium carbonate, and then degassedby bubbling nitrogen gas for 15 min. After adding Pd(PPh3)4 (57 mg,0.05 mmol) under a nitrogen atmosphere, the reaction mixturewasstirred at 80 C for 12 h, and then cooled to room temperature. Theresulting mixture was extracted with ethyl acetate three times. Thecombined organic layer was washed with deionized water anddried over sodium sulfate. After concentration under reducedpressure, the residual oil was purified by column chromatographyusing n-hexane: ethyl acetate (30: 1) as the eluent to give thedesired product as a light yellow solid in 81% yield. 1H NMR(400 MHz, DMSO-d6, d): 7.35 (t, J 2.0 Hz, 4 H), 7.30 (d, J 8.0 Hz,8 H), 7.26 (d, J 8.0 Hz, 8 H), 6.27 (s, 8 H), 1.29 (s, 36 H). 13C NMR(600 MHz, CDCl3, d): 149.92, 145.93, 134.96, 132.37, 130.58, 128.67,123.22, 115.03, 110.98, 84.10, 64.85, 28.05.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Tetrakis(4-bromophenyl)methane, and friends who are interested can also refer to it.

Reference:
Article; Yang, Yanqin; Zhang, Qiang; Zheng, Jifu; Zhang, Suobo; Polymer; vol. 54; 13; (2013); p. 3254 – 3260;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 707-34-6, 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. 707-34-6, name is 1,3,5-Tribromoadamantane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE I Synthesis of 1,3,5-Triethynyladamantane Vinyl bromide (60 mL) was added, dropwise, over 1.5 h to a solution of 1,3,5-tribromoadamantane (43 g, 115 mmol) and aluminum chloride (10 g) in CH2 Cl2 (100 mL) at a rate such that the internal temperature did not exceed -20 C. The progress of reaction, as indicated by the disappearance of 1,3,5-tribromoadamantane, was monitored by GLC and 1 H NMR. The reaction mixture was stirred at -20 C. for 1.5 hours, diluted with dichloromethane and poured slowly over crushed ice and concentrated hydrochloric acid (40 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water, dried (MgSO4) and filtered and solvent was evaporated under reduced pressure to give 80 g of crude 1,3,5-tris(2,2-dibromoethyl)adamantane. The crude material was dissolved in DMSO (350 mL) and potassium t-butoxide (80 g, 714 mmol) was added portion-wise over a period of 20 minutes. The mixture was stirred at ambient temperature for 48 h, diluted with dichloromethane and poured over crushed ice/water/concentrated hydrochloric acid (5 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water and brine, dired (MgSO4), filtered and stripped of solvent under reduced pressure to give an oil. This oil was distilled under reduced pressure (120-130 C./0.5 mm) to give 14,6 g (61%) of 1,3,5-triethynyladamantane. An analytical sample was recrystallized from pentane: mp. 84-86 C; IR 3350 and 2150 cm-1; 1 H NMR delta 2.13 (s, 3 H, C CH) and 1,96 (s, 6 H) and 1.79 (m, 7 H); Anal. Calcd for C16 H16; C, 92.26; H, 7.74. Found: C, 92.10; H, 7.79.

The synthetic route of 1,3,5-Tribromoadamantane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baum; Kurt; Archibald; Thomas G.; Malik; Aslam A.; US5017734; (1991); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 3722-78-9,Some common heterocyclic compound, 3722-78-9, name is 8-Bromochroman, molecular formula is C9H9BrO, 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-Bromochromane (17) was prepared from commercial 2,6-dibromophenol according to the literature procedure [Kerrigan, F.; Martin, C; Thomas, G.H. Tetrah. Lett. 1998, 39, 2219]. To 8-bromochromane (17) (0.1 8 g, 0.84 mmol) in dry tetrahydrofuran (2 mL) at -78 C under argon 2.5 M n-BuLi in hexanes (0.34 ml, 0.85 mmol) was added slowly. The reaction was stirred at this temperature for 30 min and then S02 (g) was bubbled through the solution for 3 minutes. The reaction was stirred at -78 C then warmed to room temperature and the solvent was evaporated. The residue was dissolved in 2 ml of DCM and NCS (0.1 12 g, 0.84 mmol) was added at r.t. , the reaction mixture stirred for 1 h, then diluted with 15 mL DCM, washed with water, brine, dried over sodium sulfate and the solvent was removed under vacuum. The residue was purified by column chromatography on silica gel (eluent petroleum ether-ethyl acetate, 3: 1 ) to give 0.054 g (30%) of compound 18. Compound was unstable under GCMS and LCMS conditions. NMR (CDCI3) delta: 7.78-7.75 (m, 1H), 7.39-7.36 (m, 1H), 6.95 (t, J=7.8 Hz, 1 H), 4.46 (t, J=5.4 Hz, 2H), 2.88 (t, J=6.5 Hz, 2H), 2.16-2.09 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 8-Bromochroman, its application will become more common.

Reference:
Patent; LATVIAN INSTITUTE OF ORGANIC SYNTHESIS; JIRGENSONS, Aigars; LOZA, Einars; CHARLTON, Michael; FINN, Paul William; RIBAS DE POUPLANA, Lluis; SAINT-LEGER, Adelaide; (76 pag.)WO2016/129983; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1311265-74-3, A common heterocyclic compound, 1311265-74-3, name is 1-Bromo-3-cyclopropyl-5-fluorobenzene, molecular formula is C9H8BrF, 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 B: A resealable glass pressure tube was charged with 2′-amino-l’,2,2-trimethyl-6-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)spiro[chroman-4,4′-imidazol]-5′( H)-one (50 mg, 0.13 mmol), 1- bromo-3-cyclopropyl-5-fluorobenzene (28 mg, 0.13 mmol), dichloro[l,l’- bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (5.3 mg, 0.0065 mmol), 20% aqueous Na2C03 (241 mu, 0.45 mmol), and 1 ,4-dioxane (1.3 mL, 0.13 mmol). The reaction mixture was sparged with N2 for 5 minutes, capped, and stirred at 90C for 90 minutes and allowed to cool to room temperature. The mixture was then diluted with EtOAc (10 mL) and washed with water (2 mL). The organic layer was separated, dried (MgSC^), filtered and concentrated in vacuo. The residue obtained was passed through a silica plug eluting with 5% MeOH/DCM to provide the semi pure product. This was then purified by preparative TLC eluting with 7% MeOH/DCM. The product isolated was filtered through a 45 muMu filter and concentrated in vacuo. The residue obtained was crystallized from DCM/Et20 to provide 2′-amino-6-(3-cyclopropyl-5-fluorophenyl)-r,2,2-trimethylspiro[chroman-4,4′-imidazol]- 5′(l’H)-one (14 mg, 0.036 mmol, 27% yield) as a solid. NMR (400 MHz, CDC13) delta 7.36 (d, J=8.61 Hz, 1H), 6.95 -6.87 (m, 4H), 6.63 (d, J=10.96Hz, 1H), 3.19 (s, 3H), 2.56 (d, J=13.03 Hz, 1H), 1.97 (d, J=14.08Hz, 1H), 1.94-1.88 (m, 1H), 1.52 (s, 3H), 1.41 (s, 3H), 1.02-0.97 (m, 2H), 0.73-0.69 (m, 2H); LCMS (APCI+) m/z 394 (M+H)+. Example 79 3-(2′-amino-1^2,2-trimethyl-5′-oxo-r,5′-dihydrospiro[chroman-4,4′-imidazole]-6-yl)-5- bromobenzonitrile

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; ARRAY BIOPHARMA INC.; HUNT, Kevin, W.; RIZZI, James, P.; COOK, Adam; WO2011/72064; (2011); 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. 40422-70-6, name is 1-Bromo-3-(2-bromoethyl)benzene, A new synthetic method of this compound is introduced below., Safety of 1-Bromo-3-(2-bromoethyl)benzene

General procedure: Thiourea (7 mmol) was dissolved in 13.5 mL ethanol and the appropriate alkylbromide (7 mmol) was added. The mixture was stirred and heated under reflux for 2 h after which the reaction became homogenous. The reaction was allowed to cool to room temperature and the ethanol solvent was removed under reduced pressure. A solution of NaOH (10.5 mmol) in 8.75 mL water was added to the residue, and the reaction mixture was heated under reflux (120 C) for 2 h. The reaction was subsequently cooled to room temperature and aqueous H2SO4 (15%) was added. The mercaptan separated as oil droplets and was extracted to diethylether (30 mL). The organic phase was washed twice with water, dried over anhydrous Na2SO4 and removed under reduced pressure. This yielded the desired mercaptans which were used without further purification for the synthesis of 1, 3 and 4.

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; Mostert, Samantha; Mentz, Wayne; Petzer, Anel; Bergh, Jacobus J.; Petzer, Jacobus P.; Bioorganic and Medicinal Chemistry; vol. 20; 24; (2012); p. 7040 – 7050;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 41825-73-4, 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. 41825-73-4, name is 2-Bromo-4,6-dimethylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Preparation of catalyst: 10mL flask was charged with a stirrer, Pd(OAc)2 (0.02mmol, 2mol%), ligand (Sym-Phos, PPh3, PhPCy2, S-Phos) (0.04mmol, 4mol%) and 1mL of THF. The flask was evacuated, backfilled with argon, and the reaction mixture was stirred for 10min at ambient temperature. Such prepared catalyst was used in the coupling reactions. Similarly were prepared catalysts based on PdCl2 complexes. Reaction setup. A round-bottom flask containing magnetic stir bar was charged with 15mL of 0.3% aqueous solution of SDS and base (3mmol). Then aryl halide (1mmol) dissolved in a minimum amount of THF, arylboronic acid or its derivative (1.5mmol) and the pre-catalyst (see above) were added. The flask was placed in to the oil bath (kept at 60C) and reaction mixture was stirred for next 16h. The product was filtered or extracted with methylene chloride or (3¡Á10mL), then combined organic layer was dried over MgSO4, filtered, solvent was evaporated and the product was isolated by column chromatography. Yields: 63-99%.

The synthetic route of 2-Bromo-4,6-dimethylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Demchuk, Oleg M.; Kap?on, Katarzyna; Mazur, Liliana; Strzelecka, Dorota; Pietrusiewicz, K. Micha?; Tetrahedron; vol. 72; 42; (2016); p. 6668 – 6677;,
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. 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole, A new synthetic method of this compound is introduced below., Safety of 5,6-Dibromobenzo[d][1,3]dioxole

A stirred solution of 5,6-dibromobenzo[d][1,3]dioxole S6 (400 mg, 1.43 mmol) in toluene (15 mL) was cooled at -78 C, and freshly distilled furan (0.51 mL, 7.15 mmol) was added to the solution. n-BuLi (1.38 M in THF, 1.14 mL, 1.57 mmol) was added dropwise to the resulting solution over 5 minutes at -78 C. The reaction mixture was stirred for 10 additional minutes before it was warmed up to -40 C. Stirringwas continued for another 2 hours before water (20 mL) was added to quench the reaction. The organic layerwas separated and the aqueous layer was extracted with Et2O (4 x 10 mL). The combined organic extracts were washed with brine (20 mL), dried over Na2SO4, and concentrated in vacuo. Purification by column chromatography on silica gel, eluting with PET/Et2O (80:20), afforded 5,8-dihydro-5,8-epoxynaphtho[2,3-d][1,3]dioxole S7 (241 mg, 1.28 mmol, 90 %) as a white crystalline solid.

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; Antien, Kevin; Viault, Guillaume; Pouysegu, Laurent; Peixoto, Philippe A.; Quideau, Stephane; Tetrahedron; vol. 73; 26; (2017); p. 3684 – 3690;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1435-54-7, 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. 1435-54-7, name is 1,3-Dibromo-2-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2: 2-(3,5-dibromo-4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane To a solution of 1,3-dibromo-2-fluorobenzene (1.43 g, 5.63 mmol) in n-heptane (100 mL) was added Pin2B2 (953 mg, 3.75 mmol), cycloocta-1,5-diene iridium salt (63 mg, 0.094 mmol) and 2,6-diisopropyl-N-(pyridin-2-ylmethylene)aniline (37 mg, 0.14 mmol). The mixture was refluxed for 4 h under N2, cooled to rt, quenched with water, extracted with EA (3*50 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography eluted with PE: EA=80:1 to give 2-(3,5-dibromo-4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.046 g, yield 49%) as solid.

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, 1,3-Dibromo-2-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Anacor Pharmaceuticals, Inc.; Eli Lilly and Company; Akama, Tsutomu; Balko, Terry William; Defauw, Jean Marie; Plattner, Jacob J.; White, William Hunter; Winkle, Joseph Raymond; Zhang, Yong-Kang; Zhou, Yasheen; US2013/131016; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary