Month: July 2021

Electric Literature of 156682-52-9, 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. 156682-52-9 name is 1,4-Dibromo-2,3-difluorobenzene, 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.

Step 1 : Synthesis of 2,3-difiuoro-1 ,4-dibromo-5,6-dinitro-benzene 2,3-difluoro-1 ,4-dibromo-benzene as the starting raw material was synthesized according to prior methods (Dunn 2006). In a 250 ml flask, concentrated sulphuric acid (50 ml) was added and cooled to 0-5C in an ice water bath. Fuming nitric acid (50 ml) and 2,3-difluoro-1 ,4-dibromo-benzene (10 g, 36.8 mmol) were slowly added. Then, the flask was heated to 65C for 14 h. The mixture was then precipitated into ice water. The resulting yellow solid was filtered and purified by column chromatograph with a mixture of hexane and dichloromethane (1 :4 v/v) to afford 2,3-difluoro-1 ,4-dibromo-5,6-dinitro- benzene (3.5 g, 26%). H and 9F NMR spectra were as expected.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,4-Dibromo-2,3-difluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; NATIONAL RESEARCH COUNCIL OF CANADA; Ll, Zhao; DING, Jianfu; LU, Jianping; TAO, Ye; WO2011/60526; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 399-94-0, 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. 399-94-0, name is 1-Bromo-2,5-difluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation A; (R)-2-(2,5-difluorophenyl)pyrrolidine; Step A: Preparation of (RVtert-butyl 2-(2.5-difluorophenyl)pyrrolidine-l- carboxylate.; A solution of tert-butyl pyrrolidine- 1-carboxylate (20 g, 116.8 mmol) and (-)- sparteine (32.9, 140 mmol) in MTBE (360 mL) was cooled to -78 0C and sec-BuU (100 mL, 140 mmol, 1.4 M in cyclohexane) was introduced drop-wise via cannula, keeping the internal temperature under -70 0C. The resulting solution was stirred for 3 hours at -78 0C, followed by addition of a solution of ZnCl2 (93.4 mL, 93.4 mmol, IM in Et2O) drop-wise with rapid stirring, keeping the internal temperature below -65 0C. The resulting light suspension was stirred at -78 0C for 30 minutes and then warmed to ambient temperature. The resulting mixture was sequentially charged with 2-bromo-l,4-difluorobenzene (14.5 mL, 128 mmol), Pd(OAc)2 (1.31 g, 5.8 mmol) and J-Bu3P-HBF4 (2.03 g, 7.0 mmol) in one portion. After stirring overnight at ambient temperature, concentrated NH4OH (10.5 mL) was added and the reaction was stirred for 1 hour. The resulting slurry was filtered through Celite and the filter cake washed with Et2O (1 L). The filtrate was washed with a IM aqueous HCl solution (0.5 L) and brine. The organic layer was filtered and concentrated, and the crude product was purified by silica column chromatography, eluting with 5-10% EtOAc/hexanes to give product (R)-tert-butyl 2-(2, 5 -difluorophenyl)pyrrolidine- 1-carboxylate as yellow oil (23.9 g, 72% yield).

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-Bromo-2,5-difluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; ANDREWS, Steven S.; CONDROSKI, Kevin Ronald; HAAS, Julia; HUANG, Lily; JIANG, Yutong; KERCHER, Timothy; SEO, Jeongbeob; WO2011/6074; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 626-39-1,Some common heterocyclic compound, 626-39-1, name is 1,3,5-Tribromobenzene, molecular formula is C6H3Br3, 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 mixture of 1,3,5-tribromobenzene (7.96 g, 25.3 mmol), bis(pinacolato)diboron (21.2 g, 83.5 mmol), [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium (2.78 g, 3.79 mmol), potassium acetate (22.3 g, 228 mmol) in anhydrous 1,4-dioxane (400 mL) was degassed for 80 minutes. Mixture was then heated to 80 C. overnight under argon. After cooling to room temperature, the remaining solids were filtered off. The filtrate was dried under vacuum, redissolved in methylene chloride (400 mL) then washed with water (2×300 mL) and brine (300 mL). Organic layer was dried over sodium sulfate and loaded onto silica gel. A silica plug (11% ethyl acetate in hexanes) and precipitation from methylene chloride/methanol gave 4 (9.76 g, 88% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3,5-Tribromobenzene, its application will become more common.

Reference:
Patent; Zheng, Shijun; US2011/196158; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 314084-61-2, name is 2-Bromo-1,3-diethyl-5-methylbenzene, 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 314084-61-2, Product Details of 314084-61-2

In a 250 mL four-necked reaction flask equipped with a stirrer, thermometer, condenser,32.0 g (0.2 mol)Diethyl malonate, 16 g (0.4 mol) of sodium hydroxide and 100 mL of N-methylpyrrolidone. (0.11111) 2,6-diethyl-4-methyl bromobenzene and 1.28 cuprous bromide were added to a solution of 120 to 130 C for 10 h. Cool, then remove the solvent under negative pressure at 0.095 MPa, 90 C, add 200 g of 7K, adjust the pH to 3 with hydrochloric acid, extract with 3 x 80 mL of ethyl acetate, wash with 3X, 150 mL water, 1 OmL was calcined and crystallized by filtration, washed with n-hexane to give 22.9 g of a pale yellow solid in 75% yield.sodium hydroxideDefinitions of sodium hydroxidenouna strongly alkaline white deliquescent compound used in many industrial processes, e.g., the manufacture of soap and paper.Primary alkaline batteries use sodium hydroxide or potassium hydroxide as the electrolyte.See alsosodium, hydroxideGoogle Translate for Business:Translator ToolkitWebsite Translator

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1,3-diethyl-5-methylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; Wuhan Institute of Technology; Liu Anchang; Dong Yuanhai; Yu Yu; Zheng Yiqian; Wang Yanlu; (10 pag.)CN106928253; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 13194-73-5, 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. 13194-73-5, name is 3,5-Dibromo-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

Example 26 1,3-Dibromo-2-methylbenzene A solution of (3,5-dibromo-4-methylphenyl)amine dissolved in water (80 mL) and concentrated HCl (7.5 mL) stirring for 20 min, then the mixture was cooled to 0~5 C., and a solution of NaNO2 (3.4 g/40 mL H2O) was added. The reaction mixture was stirred for 2 h at 0~5 C., then the suspension was added to a solution of hypophosphorous acid (50%, 27.9 g), and the mixture was cooled to 0 C. The mixture was stirred at room temperature overnight. Then it was extracted with CH2Cl2 (100 mL*2). The organic layer was washed with brine (30 mL) and dried over Na2SO4. After silica column chomatography, (eluted with petroleum ether), 3.57 g product was obtained, as a colorless liquid. 1H NMR (400 MHz, CDCl3) delta 2.57 (s, 3H), 6.89 (t, J=8.0 Hz, 1H), 7.50 (d, J=8.0 Hz, 2H).

The chemical industry reduces the impact on the environment during synthesis 3,5-Dibromo-4-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Glaxo Group Limited; US2009/203657; (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. 626-40-4, name is 3,5-Dibromoaniline, A new synthetic method of this compound is introduced below., Computed Properties of C6H5Br2N

This compound was preparedwithout the use of air and moisture sensitive protocol. Using a modifiedpreparation similar to that used by Kln and co-workers[1], aqueousformaldehyde (37%, 31.2 mL) was added to a stirring mixture of THF (300 mL)and 3M H2SO4 (84 mL) cooled to 0C in a 1 L long neck flat bottom flask. After stirring for 10minutes at 0C, 3,5 dibromoaniline (35.00 g, 139.5 mmol) dissolved in THF (75mL) was addeddropwise over 15 minutes. The solution was stirred for another 10 minutes at 0C. This mixturewas then stirred vigorously while NaBH4 (21.14 g, 558.8 mmol) was carefully added portionwiseover a period of 30 minutes at 0C. After stirring at room temperature for 2 hours the solutionwas filtered and the solid was washed with THF (30 mL). The filtrate was collected and allvolatiles were removed via rotary evaporation. The remaining residue was basified withsaturated aqueous NaHCO3 (500 mL) and extracted with dichloromethane (3 x 100 mL). Theorganic extracts were combined, washed with water (200 mL), dried with anhydrous MgSO4 andfiltered. All volatiles were removed from the filtrate via rotary evaporation and an orange-redsolid was obtained in 96 % yield (37.51 g, 134.5 mmol). Material was used without furtherpurification.

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; Smith, Joel D.; Chih, Edwina; Piers, Warren E.; Spasyuk, Denis M.; Polyhedron; vol. 155; (2018); p. 281 – 290;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 3344-70-5,Some common heterocyclic compound, 3344-70-5, name is 1,12-Dibromododecane, molecular formula is C12H24Br2, 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.

In a two-necked flask under argon, NaH (43.7 mmol) is put into suspension in anhydrous THF (100 ml). The reaction medium is cooled down in an ice bath and acetoethyl acetate is added dropwise (39.7 mmol). After stirring for 10 minutes at 0° C. n-BuLi is added dropwise (1.56 M; 43.7 mmol). Stirring is carried out for a further 10 minutes at ambient temperature before proceeding with alkylation.Dibromododecane (15.9 mmol) in solution in 20 ml of anhydrous THF is added dropwise to the previous solution. The reaction medium is allowed to return to ambient temperature and stirring is continued for 1 hour. Water is added followed by extraction with ether (3 times). The organic phase is washed with a saturated NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness. The product is purified by chromatography on silica-gel eluting with AcOEt-Hexane (1-1). A white solid is obtained (Yield=65percent); M.p.=60° C.NMR 1H (200 MHz, CDCl3): d 4.16 (q, 4H, 2CH2), 3.41 (s, 4H, 2CH2), 2.50 (t, 4H, 2CH2), 1.56-121 (m, 30H).

The synthetic route of 3344-70-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CNRS; US6972343; (2005); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 7073-94-1, A common heterocyclic compound, 7073-94-1, name is 1-Bromo-2-isopropylbenzene, molecular formula is C9H11Br, 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.

l-Bromo-2-Isopropylbenzene (6.0 g, 30 mmol) was dissolved in dry toluene (70 mL), and ethyl cyanoacetate (6.8 g, 60 mmol) and sodium phosphate (15 g, 90 mmol) were added. The reaction mixture was degassed by bubbling with argon gas. Bis(dibenzylideneacetone) palladium(O) (0.35 g, 0.60 mmol) and tri-tert-butylphosphine (0.25 g, 1.2 mmol) were added. The reaction mixture was charged in a 500 mL sealed tube and heated to 90 C for 20 hours. The reaction was cooled to room temperature and filtered through a Celite pad. The filtrate was concentrated and the residue was dissolved in ethyl acetate (120 mL) followed by a washing with water (2 x 100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography provided the title molecule as a colorless liquid (4.4 g, 63%): XH NMR (400 MHz, CDCI3) delta 7.44 (d, J = 7.6 Hz, 1H), 7.38-7.36 (m, 2H), 7.24-7.22 (m, 1H), 4.97 (s, 1H), 4.30-4.21 (m, 2H), 3.14 (hep, J = 5.2 Hz, 1H), 1.30-1.23 (m, 9H); EIMS m/z 216 ([M-CH3]+).

The synthetic route of 7073-94-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; GIAMPIETRO, Natalie C.; BAUM, Erich W.; FISCHER, Lindsey G.; GOLDSMITH, Miriam E.; CROUSE, Gary D.; RENGA, James M.; SPARKS, Thomas C.; (234 pag.)WO2016/99929; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 4117-09-3, name is 7-Bromo-1-heptene, 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 4117-09-3, Safety of 7-Bromo-1-heptene

Typical procedure for the preparation of Grignard reagent: To a suspension of magnesium (0.13g, 5.32mmol) in anhydrous THF (1mL) was added dropwise 1-bromobutane (0.1g, 0.71mmol) at room temperature under an argon. After the reaction started, a THF solution of the remaining 1-bromobutane (0.57g, 4.19mmol/anhydrous THF 4mL) was dropwise into the reaction mixture at that temperature. After stirring for 50min, 0.8M of n-BuMgBr in THF was obtained. (The concentration was determined by the titration experiment.) (0038) Method A: To a suspension of CuCN (0.059g, 0.66mmol) in anhydrous THF (1mL) was added dropwise a THF solution of n-BuMgBr (0.8M, 0.83mL, 0.66mmol, prepared from n-BuBr and magnesium) at -78C under argon. After stirring for 5min, the mixture was warmed to -10C, and then stirred for 10min. The reaction mixture was again cooled to -40C, and to this mixture was added dropwise a solution of (E)-diethyl 2-fluoro-3-phenyl-2-propenylphosphate (0.086g, 0.3mmol) in anhydrous THF (2mL). After 15min, the reaction was quenched with an aqueous saturated NH4Cl solution and the whole was extracted with diethyl ether. The combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuo. The residue was purified by silica gel column chromatography to give 2-fluoro-3-phenyl-1-heptene (13a) (quant., 19F NMR yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Bromo-1-heptene, and friends who are interested can also refer to it.

Reference:
Article; Nihei, Takashi; Kubo, Yusuke; Ishihara, Takashi; Konno, Tsutomu; Journal of Fluorine Chemistry; vol. 167; (2014); p. 110 – 121;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 176317-02-5, 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. 176317-02-5, name is 1-Bromo-2,3,4-trifluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(4-1) Synthesis of 1-(3-methyl-3-hydroxy-1-butynyl)-2,3,4-trifluorobenzene Under nitrogen replacement, 247 g of 2,3,4-trifluorobromobenzene was dissolved in 740 ml of DMF, into which 247 mL of triethylamine, 3.7 g of tetrakistriphenylphosphine palladium (0), and 4.4 g of copper iodide (I) were added, and heated to 70C. To this, 108 g of 3-methyl-1-butyne-3-ol was added dropwise for 1 hour, and the mixutre was then stirred for 2 hours at room temperature, for 1 hour at 50C, for 30 minutes at 60C, and for 2 hours at 80C. Then, 500 mL of water was added and cooled to room temperature, to which 200 mL of concentrated hydrochloric acid was added. After this was extracted twice using ethyl acetate, the extract and the organic layer were mixed together, washed using water and a saturated saline solution in that order, and dried using anhydrous magnesium sulfate. After the solvent was evaporated under a reduced pressure, the residue was purified by distillation under a reduced pressure (78 to 84C / 0.65 to 0.70 mmHg) to obtain 229 g of 1-(3-methyl-3-hydroxy-1-butynyl)-2,3,4-trifluorobenzene as a yellow solid.

The synthetic route of 1-Bromo-2,3,4-trifluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Ink and Chemicals, Incorporated; EP1640433; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary