Month: August 2021

Electric Literature of 626-40-4, These common heterocyclic compound, 626-40-4, name is 3,5-Dibromoaniline, 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.

Compound 2i was synthesized following a procedure published for the preparation of similar compounds.1 To a mixture of 3,5-dibromoaniline (0.22 g, 0.87 mmol) and Et3N (0.12 mL, 0.87 mmol) in anhydrous CH2Cl2 (10 mL), 2,2′-dithiobenzoyl chloride (1, 0.30 g, 0.87 mmol) in anhydrous CH2Cl2 (20 mL) was added dropwise over 15 min. The reaction mixture was stirred for 3 h at rt, and washed with 1 M HCl (50 mL), H2O (50 mL), and brine (50 mL). The organic layer was dried over anhydrous MgSO4, concentrated in vacuo, and the residue was purified by flash column chromatography (SiO2, 1:4/EtOAc:hexanes) and recrystallized in EtOH to afford compound 2i (135 mg, 33%, Rf 0.31 in 1:4/EtOAc:hexanes) as a white solid: 1H NMR (400MHz, CDCl3, Fig. S13) delta 8.08 (d, J = 8.0 Hz, 1H), 7.89 (s, 2H), 7.68 (t, J = 6.8 Hz, 1H), 7.58 (s,1H), 7.57 (d, J = 8.0 Hz, 1H), 7.45 (t, J = 8.0 Hz, 1H); 13C NMR (100 MHz, CDCl3, Fig. S14) delta164.3, 139.7, 139.6, 133.2, 132.5, 127.6, 126.4, 125.8, 124.5, 123.5, 120.4; LRMS m/z calcd forC13H7Br2NOS: 385.1; found 386.1 [M+H]+.

The synthetic route of 626-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ngo, Huy X.; Shrestha, Sanjib K.; Green, Keith D.; Garneau-Tsodikova, Sylvie; Bioorganic and Medicinal Chemistry; vol. 24; 24; (2016); p. S1 – S53;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 201138-91-2, 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. 201138-91-2, name is 4,6-Dibromodibenzo[b,d]furan belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

i. Weigh 32.6 mg of 4,6-dibromobenzofuran and 121 mg of the compound of formula (8) and add it to a mixed solvent containing toluene and ethanol (the volume ratio is toluene: ethanol = 12: 1),Protected by nitrogen, heated to 80 C, and reacted for 20 minutes.Then add 2mg of tris (dibenzylideneacetone) dipalladium,13 mg of bis (2-diphenylphosphine) phenyl ether and 1 ml of potassium carbonate aqueous solution (2 mol / L), heated to 95 C, and reacted for 10 hours.Stop the reaction, extract, collect the organic phase, evaporate the organic solvent under reduced pressure to obtain the crude product, and purify by column chromatography to obtain the compound of formula (VII).The eluent was a mixed solvent of chloroform and n-hexane (the volume ratio was chloroform: n-hexane = 1: 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, 4,6-Dibromodibenzo[b,d]furan, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; China Petroleum University (East China); Liu Heyuan; Yan Xinyu; Li Xiyou; (8 pag.)CN110256384; (2019); 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. 30273-40-6, name is 4-Bromo-2,5-dimethylaniline, A new synthetic method of this compound is introduced below., Product Details of 30273-40-6

Example 65-Chloro-N2-(2,5-dimethyl-4-(morpholinomethyl)phenyl)-A/4-(5-methyl-lH- pyrazol-3-yl)pyrimidine-2,4-diamine (39) [0113] Step 1: A mixture of 2,5-dichloro-N-(5-methyl-lH-pyrazol-3-yl)pyrimidin- 4-amine (732 mg, 3 mmol), 4-bromo-2,5-dimethylaniline (554 mg, 2 mmol) and cone, aqueous HCl (1.5 mL) in isopropanol (15 mL) was heated in a microwave for 40 min at 130 C. LCMS showed that the reaction was not complete, and additional 2,5- dichloro-N-(5-methyl-lH-pyrazol-3-yl)pyrimidin-4-amine (732 mg, 3 mmol) was added to the reaction. The reaction was again heated in a microwave for an additional 60 min at 130 C. The crude reaction mixture was then diluted with EtOAc (100 mL), sequentially washed with saturated aqueous NaHCO3 (2×20 mL) and brine (10 mL), dried over Na2CO3 and concentrated in vacuo. The crude product was purified by silica chromatography (0-10% MeOH in EtOAc gradient with 1% NH3 additive) to give Lambdaf2-(4-bromo-2,5-dimethylphenyl)-5-chloro-Lambda^-(5-methyl-lH-pyrazol-3- yl)pyrimidine-2,4-diamine as an off-white solid; ESMS m/z 407.2 (M+H+).

The synthetic route of 30273-40-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2009/158431; (2009); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 3814-30-0,Some common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, 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.

N-(4-(ethylsulfonyl)benzyl)-4-(propylamino)benzamide (70 mg, 0.28 mmol) was added sequentially to a 50 mL vial.Bromomethylcyclopentane(45 mg, 0.28 mmol), anhydrous potassium carbonate (115 mg, 0.83 mmol),10 mL of acetonitrile, heated to reflux for 4 hours.The reaction was completed by TLC. Spin the solvent,Wash with saturated brine and dry over anhydrous sodium sulfate.Purification of petroleum ether by column chromatography: ethyl acetate 1:2,Obtained 30mg of white solid,The yield was 23.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Bromomethyl)cyclopentane, its application will become more common.

Reference:
Patent; Fudan University; Wang Yonghui; Qiu Ruomeng; Gong Juwen; Tian Jinlong; Huang Yafei; (65 pag.)CN109206346; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 58971-11-2,Some common heterocyclic compound, 58971-11-2, name is 3-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.

N-3-brornophenethyB-2,2,2-trifhioroacetamk1e. A vial was charged with 2(3bromophenyflethanamine (600 nig, 3 mnrol). methylene chloride (2.0 mL), and tri.tluoroacetie anhydride:0 4 niL 3 mmd) lrwthvlamine (0 X4 mL 6 mmd) xas carttull iddtd dtopxs ist I Ia rcxtmn n?is stirred for 1 h then concentrated. The residue was purified on silica gel (20% EtOAc/hexanes) to provide the hUe compound (773 mg, 87% yield). LCMS: Ri? 1.007 miii; M+H 296.2..

The synthetic route of 58971-11-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VANDERBILT UNIVERSITY; CONN, Jeffrey, P.; HOPKINS, Corey, R.; LINDSLEY, Craig, W.; NISWENDER, Colleen, M.; EMMITTE, Kyle; BRONSON, Joanne; WU, Yong-Jin; PANARESE, Joe; ENGERS, Darren, W.; ENGERS, Julie; (136 pag.)WO2016/123627; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1435-53-6, 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. 1435-53-6, name is 2,4-Dibromo-1-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Dibromofluorobenzene (1.0 g, 4.0 mmol), sodium methanethiolate (0.33 g, 4.8 mmol) and triethylamine (0.52 mL, 4.0 mmol) were dissolved in a flask charged with 3 mL of N,N-dimethylacetamide in a sealed tube and heated to 100 C for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature, extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and passed through a silica gel column (ethyl acetate / n-hexane) to give an oily liquid (0.65 g, 58%).

The synthetic route of 2,4-Dibromo-1-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; South China University of Technology; Yang Wei; Yang Yong; Zhang Bin; Wu Hongbin; Cao Yong; (32 pag.)CN105001233; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 103-64-0,Some common heterocyclic compound, 103-64-0, name is (2-Bromovinyl)benzene, molecular formula is C8H7Br, 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.

S1: To the appropriate amount of organic solvent DMF, 100 mmol of the compound of the above formula (I), 150 mmol of the compound of the above formula (III), 150 mmol of the amine source cerium ammonium nitrate, 2 mmol of the catalyst dinitrodiammine platinum, 5 mmol of the ligand (3-cyanopropyl) imidazole chloride and 200 mmol sodium hexametaphosphate were added and the temperature was raised to 60 C and the reaction was stirred at that temperature for 8 hours. S1DMF100mmol(I)150mmol(III)150mmol2mmol5mmolL120mmol1,3-(3-)200mmol60C8 Submit CorrectionsCloseS2: After the reaction of step S2 was completed, an aqueous solution of acetic acid having a mass percentage of 20% was added dropwise to the resulting system until the total molar amount of acetic acid added was 200 mmol, and the reaction was stirred at 60 C for 80 minutes. S2S220200mmol60C80 Submit CorrectionsCloseAfter completion of the reaction at step S2, the mixture was poured into ethyl acetate, washed successively with saturated aqueous NaHCO3 and brine, and the aqueous layer was extracted with ethyl acetate. The washed organic layers and the extracted organic layers were combined with anhydrous Na2 SO 4, and the solvent was distilled off under reduced pressure. The residue was purified by flash column chromatography (using n-hexane-ethyl acetate mixture as eluent, volume ratio of 1: 1) to give the compound of the above formula (III) The yield was 95.1%.

The synthetic route of 103-64-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Bokang Fine Chemical Co., Ltd.; Fu Zhiwei; (11 pag.)CN104876871; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 129316-09-2, These common heterocyclic compound, 129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene, 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 1 : 1-Bromo-3-(tert-butyl)-5-(prop-1-en-2-vnbenzene (P24a)To a solution of 1 ,3-dibromo-5-(terf-butyl)benzene (2.92 g, 10 mmol) in dioxane (20 mL) was added Pd(PPh3)4 (3.0 g, 2.6 mmol), prop-1-en-2-ylboronic acid (1.0 g, 12 mmol), K2C03 (2.8 g, 20 mmol) and H20 (1 mL) under N2. The resulting mixture was stirred at 90C overnight, concentrated and purified by CC (hexane) to give compound P24a (2.5 g, 100%; 80% by GC/MS) as a liquid.

Statistics shows that 1,3-Dibromo-5-(tert-butyl)benzene is playing an increasingly important role. we look forward to future research findings about 129316-09-2.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas; WO2012/139775; (2012); 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. 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1,3-Dibromo-5-fluorobenzene

EXAMPLE 5 (3-Bromo-5-fluorophenyl)-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one Procedure B A mixture of (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid (2.22 g, 10 mmol), 1,3-dibromo-5-fluorobenzene (3.05 g, 12 mmol), tetrakis(triphenylphosphine)palladium (0) (0.6 g, 0.52 mmol), and sodium carbonate (2.2 g, 21 mmol) in a mixture of DME and water (70 mL/15 mL) was degassed to remove the oxygen and then heated at 85 C. under a blanket of nitrogen for 3 hours. The reaction mixture was cooled to ambient temperature and quenched with a saturated aqueous ammonium chloride solution (20 mL). Ethyl acetate (100 mL) was added and organic layer was separated. The aqueous layer was extracted with ethyl acetate (3*30 mL). The combined organic layers were washed with brine and dried with MgSO4. The solvent was removed in vacuo and the residue was purified by a silica gel flash chromatography (hexane:ethyl acetate/1:1) to give 6-(3-bromo-5-fluorophenyl)-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one as a white solid (1.4 g, 40%): mp 182-183 C.; 1H-NMR (DMSO-d6) delta10.36 (s, 1H, D2O exchangeable), 7.78 (s, 1H), 7.58-7.65 (m, 3H), 7.49 (dd, 1H, J=8.3, 1.8 Hz), 6.96 (d, 1H, J=8.5 Hz), 1.69 (s, 6H); 19F-NMR (DMSO-d6) delta-112.46 (m, 1F); MS (CI) m/z 352([M+H]+, 78%), 350([M+H]+, 75%). Anal. Calc. For C16H13BrFNO2: C, 54.88; H, 3.74; N, 4.00. Found: C, 54.83; H, 3.82; N, 3.95.

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; Wyeth; Ligand Pharmaceuticals, Inc.; US6436929; (2002); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 3972-64-3, A common heterocyclic compound, 3972-64-3, name is 1-Bromo-3-(tert-butyl)benzene, molecular formula is C10H13Br, 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.

A 1. 6 M solution of”butyllithium (0.85 mL, 1.36 mmol) was added to a solution of dicyclohexylamine (0.27 mL, 1.36 mmol) in toluene (5 mL). After stirring for 5 min, a mixture of cisltrans isomers of 3-methyl-cyclohexanecarboxylic acid 2- trimethylsilanyl-ethyl ester (269 mg, 1.11 mmol) was added. After stirring for 30 min, 1-bromo-3-tert-butyl-benzene (250 mg, 1.17 mmol) was added followed by the simultaneous addition of tri-tert-butylphosphonium tetrafluoroborate (31 mg, 107 pmol) and tris (dibenzylideneacetone) dipalladium (0)-chloroform adduct (54 mg, 52.2 pmol). The solution was placed into a preheated oil bath at 60 °C. After stirring for 20 h, the solution was diluted with 10percent aqueous hydrochloric acid, and extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was flash chromatographed with 49: 1,24 : 1, and 23: 2 hexanes: ethyl acetate as the eluant to yield 250 mg (62percent yield) of a mixture of cisltrans isomers of 1- (3-tert-butyl-phenyl)- 3-methyl-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester as a yellow oil. Method [2] Retention time 3.64 min by HPLC and 3.68 min by MS (M+Na=397).

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; ELAN PHARMACEUTICALS, INC.; WO2005/70407; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary