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. 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

Application of 57190-17-7,Some common heterocyclic compound, 57190-17-7, name is 2-Bromo-1,3-diisopropylbenzene, molecular formula is C12H17Br, 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.

Add 2.92 g (0.12 mol) of magnesium shoulder and 0.05 g of crystalline iodine to a 250 mL four-neck round bottom flask under nitrogen24. A solution of lg (0.1 mol) of 2,6-diisopropylbromobenzene, 34.5 g (0.15 mol) of n-butyl borate and 75 mL of anhydrous tetrahydrofuran was dropped into the flask. The temperature of the water bath was 25 C, the reaction started, the color of iodine disappeared, and the temperature of the solution increased. Adjust the drop rate to keep the temperature of the solution at around 30 C, about 1 hour. After the completion of the dropwise addition, the mixture was stirred for 1 hour to obtain a solution 2. The solution 2 was poured into 100 mL of 4 wt.% of 0″ hydrochloric acid and stirred for 30 min. After standing, the organic layer was separated, and the aqueous layer was extracted with diethyl ether (100 mL×3 times). The organic layer was combined and the solvent was evaporated under reduced pressure. The water was adjusted to RhoEta=10 with sodium hydroxide solution. The butanol and the like were removed by steam distillation under reduced pressure (40-50 C), filtered while hot, and the filtrate was acidified to pH Eta = 2, crystals were precipitated, cooled, and suction filtered. Dry to constant weight.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1,3-diisopropylbenzene, its application will become more common.

Reference:
Patent; Nanjing Medical University; Li Fei; Chen Dongyin; Yang Lei; Dong Zezhong; Zhou Yu; Luo Chunxia; Jiang Nan; Li Tingyou; Qin Yajuan; (6 pag.)CN108774254; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 402-43-7, A common heterocyclic compound, 402-43-7, name is 1-Bromo-4-(trifluoromethyl)benzene, molecular formula is C7H4BrF3, 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.

i-Butyl piperazine-l-carboxylate (1.52 g, 8.17 mmol, 2.00 equiv), l-bromo-4- (trifluoromethyl)benzene (1 g, 4.10 mmol, 1.00 equiv), BINAP (124 mg, 0.40 mmol, 0.10 equiv), Pd2(dba)3 (184 mg, 0.20 mmol, 0.05 equiv), NaOi-Bu (1.2 g, 12.50 mmol, 3.00 equiv), and toluene (15 mL) were combined in a 100-mL round- bottom flask, stirred overnight at 100C in an oil bath, and concentrated under vacuum. Purification by silica gel column with PE/EA (50:1) yielded 1.06 g (78%) of i-butyl 4-(4-(trifluoromethyl)phenyl)piperazine-l-carboxylate as a yellow solid.LC-MS (ES, m/z): 331 [M+H]+

The synthetic route of 402-43-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOENERGENIX; MCCALL, John, M.; MCKEARN, John; ROMERO, Donnal, L.; CLAIR, Michael; WO2011/28947; (2011); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 2789-89-1,Some common heterocyclic compound, 2789-89-1, name is 1,2-Bis(4-bromophenyl)ethyne, molecular formula is C14H8Br2, 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.

The starting material 2-aminobenzamide (0.3 mmol, 1 equiv),4,4′-dibromodiphenylacetylene (0.9 mmol,3equiv), catalyst palladium trifluoroacetate (Pd(TFA) 2, 0.03 mmol, 10%) and ligand 2,2′-bipyridine (bpy,0.06mmol, 20%) was added to the reaction vessel, and the reaction vessel was continuously subjected to three pumping-oxygenation operations, and then continued.The reaction solvent 1,4-dioxane (1,4-dioxane, 0.4 mL) was added to the reaction vessel, followed by reaction at 100 C in an oil bath.Stir at temperature until the end of the reaction (about 12h), then spin off the reaction solvent and pass column chromatography (filled with 300 mesh in column)400 mesh silica gel, separated by dichloromethane and ethyl acetate in a volume ratio of 10:1 as an eluent), after separation and purification, whiteSolid, yield 79%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Bis(4-bromophenyl)ethyne, its application will become more common.

Reference:
Patent; Wenzhou University; Liu Miaochang; Liu Wei; Bi Kang; Zhu Xiaobin; Gao Wenxia; Huang Xiaobo; Wu Huayue; (11 pag.)CN108129402; (2018); A;,
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. HPLC of Formula: C6H11Br

General procedure: A 70 ml oven dried autoclave containing a stirrer bar wascharged the AgI (0.5 mg, 0.002 mmol) and Cs2CO3 (978 mg, 3.0mmol). The autoclave was purged three time with CO2 and theterminal alkynes 1 (2.0 mmol), bromides 2 (3.0 mmol), and dryDMF (20 ml) were then added sequentially via a syringe. Theautoclave was then sealed and pressurized to the appropriatepressure with CO2. The reaction mixture was then stirred at 60C for 24 h and the autoclave was cooled to room temperatureand the remaining CO2 slowly vented from the system. Thereaction mixture was diluted with water (30 ml) and extractedwith ethyl acetate (30 ml × 3). The combined organic layerswere washed with water and brine, dried over Na2SO4, andfiltered. The solvent was removed under vacuum. The productwas isolated by column chromatography on silica gel.

The synthetic route of 6-Bromo-1-hexene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Linlin; Zhang, Wenzhen; Shi, Linglong; Ren, Xiang; Lue, Xiaobing; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 34; 6; (2013); p. 1179 – 1186;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 10269-01-9, name is (3-Bromophenyl)methanamine, 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 10269-01-9, Safety of (3-Bromophenyl)methanamine

General procedure: N,N’-di(2-fluorophenyl)-4-methoxyl-isophthalamide(1a): Equipped a stirrer in a three-necked flask (100 ml), to a mixture of 2-fluoroaniline (1.11 g, 10.0 mmol),anhydrous tetrahydrofuran (15 ml) and dry pyridine (1 ml), dropwise added 4-methoxyl-isophthaloyl dichloride (1.17 g, 5.0 mmol) which had been dissolved in dry tetrahydrofuran (10 ml). After the mixture reaction at room temperature for 8 h under continuous stirring, the excess tetrahydrofuran was distilled off in vacuum. The residue was recrystallized by acetone. Its melting point is 204-206 C, and yield is 67%. The other compounds 1b-1j, 2a-2k, 3a-3l and 4a-4h were prepared in the same manner.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (3-Bromophenyl)methanamine, and friends who are interested can also refer to it.

Reference:
Article; Liu, Xiu Jie; Shi, Xin Xin; Zhong, Yong Liang; Liu, Ning; Liu, Kai; Bioorganic and medicinal chemistry letters; vol. 22; 21; (2012); p. 6591 – 6595,5;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1647-26-3, A common heterocyclic compound, 1647-26-3, name is 1-Bromo-2-cyclohexylethane, molecular formula is C8H15Br, 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: The compounds were prepared according to the procedure previouslydescribed.19,30 To a refluxing solution of thiazolidine-2,4-dione (43 mmol) in ethanol (25 mL) was added a hot solutionof potassium hydroxide (45 mmol) in ethanol (25 mL). After additionalrefluxing for 30 min, the mixture was cooled to room temperatureand the precipitate was filtered and washed with coldethanol. The obtained potassium 2,4-dioxothiazolidin-3-ide (2)(5 mmol) was refluxed with alkyl halides (5.5 mmol) in DMF(15 mL) for 3-4 h. After cooling to room temperature and additionof water (50 mL), the crude product was extracted 3 times withethyl acetate, washed with brine, and purified by flash chromatography(cyclohexane/ethyl acetate).

The synthetic route of 1647-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bastos Lima, Allan; Behnam, Mira A.M.; El Sherif, Yasmin; Nitsche, Christoph; Vechi, Sergio M.; Klein, Christian D.; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5748 – 5755;,
Bromide – Wikipedia,
bromide – Wiktionary

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 4549-33-1, name is 1,9-Dibromononane, This compound has unique chemical properties. The synthetic route is as follows., category: bromides-buliding-blocks

Preparation 103 (R)-4-(Biphenyl-2-ylcarbamoyloxy)-1-(9-bromononyl)-1-azoniabicyclo[3.2.1]octane Bromide To a stirred solution of the product of Preparation 102 (1.21 g, 3.76 mmol) and triethylamine (1.05 ML, 7.52 mmol) in acetonitrile (18.8 ML) was added 1,9-dibromononane (994 muL, 4.89 mmol) and the reaction mixture was heated at 50 C. for 4 h.The reaction mixture was then cooled and the solvent was removed under reduced pressure.The residue was dissolved in dichloromethane (20 ML) and the organic layer was washed with saturated aqueous sodium bicarbonate (10 ML), dried (magnesium sulfate) and solvent removed under reduced pressure.The crude product was purified by flash chromatography (10% methanol/dichloromethane, 0.5% ammonium hydroxide) to give the title compound (1.04 g, 1.97 mmol, 52% yield).

According to the analysis of related databases, 4549-33-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mammen, Mathai; Dunham, Sarah; Hughes, Adam; Lee, Tae Weon; Husfeld, Cralg; Stangeland, Eric; US2004/167167; (2004); 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. 58971-11-2, name is 3-Bromophenethylamine, A new synthetic method of this compound is introduced below., name: 3-Bromophenethylamine

2-(3-Bromo-phenyl)-ethylamine (0.5 mmol) and formaldehyde (2.5 mmol) were mixed in 5 ml of 1,2-dichloroethane in a process vial, which was sealed with a septum. Sodium triacetoxyborohydride (1 mmol) was added under argon atmosphere. The suspension was subjected to microwave irradiating conditions (CEM Discover equipped with a CEM Explorer automated reaction handling module). The reaction mixture was heated for 5 min at 120C and then cooled. The crude was evaporated to dryness and then suspended in aqueous NaHCO3. The product was extracted with CH2Cl2 and washed with aqueous NaHCO3. The CH2Cl2 extract was dried with anhydrous Na2SO4, filtered and evaporated to dryness to give the crude product [2-(3-bromo-phenyl)-ethyl]-dimethyl-amine. The crude was purified by flash column chromatography (CH2Cl2-MeOH as eluents) by using a CombiFlash Companion system to yield the title compound (86%) as colourless oil.

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; Laboratorios del Dr. Esteve S.A.; EP1997493; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary