Author: Jessica.F

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. 70733-25-4, name is 3-Bromo-5-methylbenzene-1,2-diamine, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-5-methylbenzene-1,2-diamine

A round bottom flask is charged with 1g (4.97 mmol) 3-Bromo-5-methyl-benzene-1 ,2- diamine and solved into 27 ml EtOH. 1.23 g (4.97 mmol) 3,4,5-trimethylphenylglyoxal monohydrate is then added and the mixture is heated to 600C for 1 h. After cooling to O0C, the title compound is collected by filtration and used in the next step without further purification.

The synthetic route of 70733-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2008/148867; (2008); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 10485-09-3, The chemical industry reduces the impact on the environment during synthesis 10485-09-3, name is 2-Bromoindene, I believe this compound will play a more active role in future production and life.

A solution of (pS)-9 (2.00g, 4.04mmol) in THF (70mL) was cooled to -78C, treated with nBuLi (1.6M in hexanes, 3.03mL, 4.85mmol) and stirred at -78C for 30min. A solution of ZnCl2 (0.5M in THF, 9.70mL, 4.85mmol) was added dropwise, the solution warmed to rt over 30min and stirred at rt for 1h. Next, Pd(PPh3)2Cl2 (0.140g, 0.200mmol) in THF (5mL) was treated with DIBAL (1M in THF, 0.400mL, 0.440mmol), stirred for 5min and added dropwise via cannula to the reaction. The resultant solution was heated at reflux and a solution of 2-bromoindene42 (1.56g, 8.08mmol) in THF (5mL) added dropwise over 30min. After refluxing for 4d the solution was cooled to rt, quenched with NH4Cl(aq) (10mL), washed with water (2×40mL), brine (40mL), dried over MgSO4 and concentrated in vacuo. Purification was achieved using flash column chromatography (pet. ether) to give the title compound as an orange oil (1.47g, 75%). Rf=0.31 (pet. ether); [alpha]25D=+235.3[alpha]D25=+235.3 (c 1.02, CHCl3); IR numax 2943, 2866, 1461, 1391, 1130, 1105, 1057, 999, 908, 882cm-1; 1H NMR (400MHz) delta 1.18-1.70 (21H, m, Si(iPr)3), 3.72 (1H, d, J=22.8, IndCH2), 3.79 (1H, d, J=22.8, IndCH2), 4.07 (5H, s, Cpunsub), 4.26 (1H, app t, J=2.5, Cpsub), 4.42 (1H, dd, J=2.5, 1.5, Cpsub), 4.48 (1H, dd, J=2.5, 1.5, Cpsub), 4.74 (1H, d, J=11.6, CpCH2), 4.95 (1H, d, J=11.6, CpCH2), 7.08 (1H, s, IndCH), 7.16 (1H, app dt, J=7.2, 0.8, ArH), 7.25 (1H, app t, J=7.2, ArH), 7.31 (1H, d, J=7.2, ArH), 7.45 (1H, d, J=7.2, ArH); 13C NMR (100MHz) delta 12.2 (CH), 18.2 (CH3), 41.0 (CH2), 61.4 (CH2), 67.3 (CH), 69.0 (CH), 69.7 (CH), 70.9 (CH), 81.4 (C), 85.0 (C), 120.1 (CH), 123.4 (CH), 123.8 (CH), 126.4 (CH), 126.6 (CH), 142.7 (C), 145.5 (C), 146.2 (C); m/z (EI+) 510 (10%, M++HNa), 509 (26%, M++Na), 314 (23%, M++H-OTIPS), 313 (100%, M+-OTIPS), 301 (15%, M+-COTIPS), 269 (7%); HRMS C29H38FeNaOSi calcd 509.1934, found 509.1903; Anal. Calcd for C29H38FeOSi: C, 71.59; H, 7.87. Found: C, 71.10; H, 7.81.

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

Reference:
Article; Anderson, James C.; Grounds, Helen; Szaloki, Gyoergy; Tetrahedron Asymmetry; vol. 24; 17; (2013); p. 1023 – 1034;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 33070-32-5, A common heterocyclic compound, 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, molecular formula is C7H3BrF2O2, 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.

EXAMPLE 79A 2,2-difluoro-1,3-benzodioxol-5-ylboronic acid A solution of 1.5M tert-butyllithium in pentane (130 mL, 195 mmol) in diethyl ether (500 mL) at -78 C. was treated with 5-bromo-2,2-difluoro-1,3-benzodioxole (18 g, 76 mmol) in diethyl ether (80 mL), stirred for 1 hour, treated with triisopropylborate (37 mL, 160 mmol), warmed to room temperature over 1 hour, poured into 4M NaOH (700 mL), stirred for 15 minutes, cooled, adjusted to pH 1 with concentrated HCl, and extracted with ethyl acetate. The extract was washed with brine, dried (Na2SO4), filtered, and concentrated to provide 14.7 g (95%) of the desired product. 1H NMR (DMSO-d6) delta7.75 (m, 1H), 7.66 (m, 1H), 7.51 (m, 1H), 7.39 (m, 1H), 7.30 (m, 1H).

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; Claiborne, Akiyo K.; Gwaltney II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2003/87940; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 100189-84-2, 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. 100189-84-2, name is 2,5-Dibromo-1,3-dimethylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: 3-(4-Bromo-3,5-dimethylphenyl)furan A mixture of 2,5-dibromo-1,3-dimethylbenzene (2.00 g), 1-furan-3-ylboronic acid (856 mg), and 2 M aqueous Na2CO3 solution (11 mL) in 1,4-dioxane (40 mL) is purged with argon for 5 min. Tetrakis-triphenylphosphine-palladium-(0) (270 mg) is added and the mixture is stirred at 100 C. over night. More tetrakis-triphenylphosphine-palladium-(0) (50 mg) is added and the mixture is stirred for another 5 h at 100 C. After cooling to room temperature the mixture is diluted with ethyl acetate and aqueous NH4Cl solution. The aqueous phase is extracted with ethyl acetate and the combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0?90:10) to give the title compound. LC (method 7): tR=1.22 min; Mass spectrum (EI+): m/z=250 [M]+.

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, 2,5-Dibromo-1,3-dimethylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim International GmbH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; US2013/252937; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1435-53-6, 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. 1435-53-6 name is 2,4-Dibromo-1-fluorobenzene, 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.

General procedure: 8.7 1,3-Di(2-thienyl)-4-fluorobenzene (11g): Starting with 10 (100 mg, 0.39 mmol), Cs2CO3 (190 mg, 0.50 mmol), Pd(PPh3)4 (3 mol%), 2-thienylboronic acid (49 mg, 0.39 mmol) and 1,4-dioxane (4 mL), 11g was isolated as a colorless solid (49 mg, 48%). Mp 91-93 C. 1H NMR (300 MHz, CDCl3): delta = 7.00-7.06 (m, 2H, ArH), 7.22-7.34 (m, 5H, ArH), 7.41-7.43 (m, 1H, ArH), 7.52-7.57 (m, 1H, ArH). 13C NMR (75.46 MHz, CDCl3): delta = 113.4 (d, J = 24.5 Hz, CH), 121.1 (d, J = 13.5 Hz, C), 121.8 (d, J = 3.1 Hz, CH), 123.8 (CH), 125.6 (CH), 125.8 (d, J = 4.5 Hz, CH), 126.3 (d, J = 7.1 Hz, CH), 127.8 (CH), 128.3 (CH), 129.0 (d, J = 4.2 Hz, CH), 134.9 (d, J = 9.4 Hz, C), 136.9 (d, J = 3.87 Hz, C), 142.6 (d, J = 2.9 Hz, C), 159.2 (d, JCF = 250.2 Hz, CF). 19F NMR (282.4 MHz, CDCl3): delta = -107.4 (CF). IR (ATR, cm-1): , 3067 (w), 2956 (w), 2871 (w), 1886 (w), 1799 (w), 1724 (w), 1605 (w), 1555 (w), 1484 (w), 1421 (w), 1355 (w), 1289 (w), 1244 (w), 1177 (w), 1121 (w), 1071 (w), 999 (w), 960 (w), 866 (w), 841 (w), 808 (m), 746 (w), 696 (m), 613 (w), 561 (w), 529 (w). GC-MS (EI, 70 eV); m/z (%) = 260 (100) [M]+, 215 (13). HRMS (EI) calcd. for C14H9FS2 [M]+: 260.01242; found 260.01360.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dibromo-1-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Article; Sharif, Muhammad; Maalik, Aneela; Reimann, Sebastian; Feist, Holger; Iqbal, Jamshed; Patonay, Tamas; Villinger, Alexander; Langer, Peter; Journal of Fluorine Chemistry; vol. 146; (2013); p. 19 – 36;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 955959-84-9, 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. 955959-84-9 name is 4-(4-Bromophenyl)dibenzo[b,d]furan, 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.

Under argon atmosphere, 8 · 31g (10mmol) of Intermediate B-1, 6.46g (20mmol) 4- (4-bromophenyl) dibenzofuran, 0.28g (0.3mmol) of tris (dibenzylideneacetone yl) dipalladium, 0.174 g (0.6 mmol) of tri-tert-butylphosphine tetrafluoroborate and 3.8g (20mmol) sodium tert-butoxide into the three-necked flask, followed by addition of 50ml of dry xylene was heated under reflux for 8 hours The Cooled to 50 ° C, filtered through celite / silica gel, and the filtrate was concentrated under reduced pressure. The resulting residue was purified on a silica gel column and then recrystallized from toluene to give 6.48 g of solid, which was compound BS1 in a yield of 78percent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(4-Bromophenyl)dibenzo[b,d]furan, and friends who are interested can also refer to it.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Zhou Wenting; Cai Hui; (24 pag.)CN106946865; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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 68322-84-9 as follows. COA of Formula: C7H3BrF4

Example 34a 2-bromo-1-(2,4-difluorophenoxy)-4-(trifluoromethyl)benzene A mixture of 3-bromo-4-fluorobenzotrifluoride (0.5 mL, 3.52 mmol), 2,4-difluorophenol (0.337 mL, 3.52 mmol), and potassium carbonate (0.486 g, 3.52 mmol) in dimethylformamide (7 mL) was heated at 80 C. overnight. The reaction mixture was cooled to ambient temperature and partitioned between ethyl acetate and water. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organics were washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation. The crude material was purified by flash chromatography (ethyl acetate/hexanes) to provide the title compound (1.0 g, 80% yield).

According to the analysis of related databases, 68322-84-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hasvold, Lisa A.; Liu, Dachun; McDaniel, Keith F.; Pratt, John; Sheppard, George S.; Wada, Carol K.; Woller, Kevin R.; US2014/256705; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, molecular formula is C7H3BrF4, 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. Application In Synthesis of 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene

Reference Example 54 1-[2-fluoro-4-(trifluoromethyl)phenyl]pyrrolidin-3-ol; A solution of 1-bromo-2-fluoro-4-(trifluoromethyl)benzene (4.6 g), 3-hydroxypyrrolidine (1.5 g), palladium(II) acetate (137 mg), (+/-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.07 g) and cesium carbonate (16.8 g) in toluene (90 mL) was stirred under an argon gas atmosphere at 85C for 16 hr. After cooling to room temperature, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate 90:10 – 65:35) to give the title compound (2.82 g, yield 66%) as a gray solid. 1H-NMR (300 MHz, CDCl3) delta:1.63 (d, J = 4.5 Hz, 1 H), 1.96 – 2.22 (m, 2 H), 3.40 – 3.57 (m, 2 H), 3.61 – 3.81 (m, 2 H), 4.51 – 4.66 (m, 1 H), 6.64 (t, J = 9.1 Hz, 1 H), 7.15 – 7.25 (m, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 40161-54-4, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2295406; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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 69321-60-4 as follows. name: 2,6-Dibromotoluene

To the solution of 2,6-dibromotoluene (55.5 g, 222.1 mmol) and NBS (43.5 g, 244.3 mmol) in carbon tetrachloride (300 mL) was added benzoyl peroxide (5.37 g, 22.2 mmol). The reaction mixture was refluxed for 20 h, cooled to room temperature, washed with water (300 mL×3) and brine (300 mL) and dried over anhydrous sodium sulfate. The solution was filtered and evaporated to give 1,3-dibromo-2-bromomethylbenzene as a yellow power (71 g). This material was used for next step without further purification.

According to the analysis of related databases, 69321-60-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Billedeau, Roland Joseph; Kondru, Rama K.; Lopez-Tapia, Francisco Javier; Lou, Yan; Owens, Timothy D.; Qian, Yimin; So, Sung-Sau; Thakkar, Kshitij C.; Wanner, Jutta; US2012/295885; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 51376-06-8,Some common heterocyclic compound, 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole, molecular formula is C6H3BrN2O, 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.

5-bromo-2,1,3-benzoxadiazole (0.17 g) (which can be prepared according to Org. Proc. Res. Dev., (2003), 7, 436-445 at page 437), triethylamine (0.11 g) and dichlorobistriphenyl-phosphine palladium (II) (0.12 g) were added to a solution of N- ({(5S)-3-[3-fluoro-4-(trimethylstannyl)phenyl]-2-oxo-1,3-oxazolidin-5- yl}methyl)acetamide (0.18 g) (which can be prepared according to Example 8 of WO 01/94342, page 52) in dry dimethyl formamide (15 mL) and the reaction mixture was heated at 100 C for about 3 hours, cooled and diluted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated. The crude product was purified by column chromatography using 2 % methanol in dichloromethane as eluent to yield the title compound (0.14 g). Melting point: 156-165 C; EMS (m/z): 388 (M+H); 1HNMR(CDCB): delta 7.91 (m, 2H), 7.62 (m, 2H), 7.52 (t, 1H), 7.35 (dd, 1H), 6.10 (t, 1H), 4.84 (m, 1H), 4.12 (t, 1H), 3.87 (t, 1H), 3.71 (m,2H), 2.02 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromobenzo[c][1,2,5]oxadiazole, its application will become more common.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2006/35283; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary