Author: Jessica.F

Reference of 14922-91-9, A common heterocyclic compound, 14922-91-9, name is 5-Bromo-2-ethylaniline, molecular formula is C8H10BrN, 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 2: Preparation of 4-bromo-1-ethyl-2-iodobenzeneTo a stirred mixture of 5-bromo-2-ethylaniline (3.39 g, 200 mmol) in distilled water (110 ml) is added concentrated sulfuric acid (5.60 ml), followed by brief heating at reflux until dissolution. The mixture is allowed to cool to room temperature, producing a fine precipitate, then further cooled to approximately 0 C. in an ice/salt bath. To this slurry is added an aqueous solution of sodium nitrite (1.17 g, 16.94 mmol) in distilled water (10 ml) dropwise over 15 minutes, maintaining a temperature below 5 C., followed by additional stirring for 30 minutes. The reaction mixture is next filtered then added to a second solution of aqueous potassium iodide (8.44 g, 50.83 mmol) in distilled water (45 ml) dropwise at room temperature. After the addition is complete the solution is briefly heated to 80 C. then allowed to cool to room temperature again. The reaction mixture is extracted with ethyl acetate (3×50 ml), and the organic phase is washed with 1M aqueous hydrochloric acid (30 ml) and aqueous sodium thiosulfate (2×30 ml). After drying over anhydrous magnesium sulfate and concentration in vacuo 4-bromo-1-ethyl-2-iodobenzene (4.90 g) is furnished as an orange liquid.

The synthetic route of 14922-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA CROP PROTECTION LLC; US2012/190545; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 7073-94-1, name is 1-Bromo-2-isopropylbenzene, 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 7073-94-1, Product Details of 7073-94-1

To a solution of 1-bromo-2-isopropylbenzene (300 mg, 1.51 mmol) in dry THF (4.0 mL) cooled at -78 C, n-BuLi (1.6 M in n-hexane, 1.04 mL, 1.66 mmol) was added dropwise over 20 min. The mixturewas stirred for 15 min and dry DMF (128muL, 1.66 mmol) was slowly added at -78 C. After 15 minthe temperature was raised up to -10 C and water was added. The mixture was extracted 3 timeswith dichloromethane (5 mL), and the combined organic layers were dried over anhydrous Na2SO4,filtered and concentrated. The residue was purified by flash chromatography on silica gel (1:20 ethylacetate/petroleum ether), to give 10SI as a colorless oil (61% yield). 1H NMR (300 MHz, CDCl3): delta10.36 (s, 1H), 7.81 (d, 1H, J = 7.8 Hz), 7.55 (t, 1H, J = 7.5 Hz), 7.44 (d, 1H, J = 4.8 Hz), 7.34 (t, 1H, J =7.5 Hz), 4.01 – 3.95 (m, 1H), 1.32 (s, 3H), 1.25 (s, 3H).

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

Reference:
Article; D’Alessandro, Sarah; Alfano, Gloria; Di Cerbo, Luisa; Brogi, Simone; Chemi, Giulia; Relitti, Nicola; Brindisi, Margherita; Lamponi, Stefania; Novellino, Ettore; Campiani, Giuseppe; Gemma, Sandra; Basilico, Nicoletta; Taramelli, Donatella; Baratto, Maria Camilla; Pogni, Rebecca; Butini, Stefania; Bioorganic Chemistry; vol. 89; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 21120-91-2, name is 7-Bromobicyclo[4.2.0]octa-1,3,5-triene, 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: C8H7Br

To a stirred solution of mercury(II) oxide (591.3 mg, 2.73 mmol) and 35 % aqueous tetrafluoroboric acid (TFBA) (999.4 mg, 5.46 mmol) in 1,4-dioxane (10.9 mL), 1- bromobenzocyclobutene (1.0 g, 5.46 mmol) was added. The reaction stirred at room temperature for 2 h and was then treated successively with NaHCO3 and 3N KOH until the solution remained basic. The precipitated mercury(II) oxide was filtered off and the filtrate extracted with CH2Cl2 (3 x 300 mL), dried with anhydrous Na2SO4, filtered, and concentrated to yield white crystals that were purified via column chromatography using a 3:2 Hexanes:EtOAc solvent system.

The synthetic route of 7-Bromobicyclo[4.2.0]octa-1,3,5-triene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VANDERBILT UNIVERSITY; WO2008/24435; (2008); A2;,
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. 75024-22-5, name is 1,4-Dibromo-2,3-dimethylbenzene, A new synthetic method of this compound is introduced below., Computed Properties of C8H8Br2

General procedure (a): A solution of 1,2-dimethylaryle 2b-e,h (10 mmol) and finely pulverised N-bromosuccinimide (NBS 3.68 g, 21 mmol, 2.1 equiv) in CCl4 (40-80 mL) was irradiated with HPK125 mercury lamp for 1-2 h with good stirring (tlc or 1H NMR monitoring). The reaction mixture was diluted with CH2Cl2, washed with H2O or 2 N aqueous NH4Cl solution and dried over MgSO4. The solvent was evaporated to give quantitatively 5b-e,h which was used without further purification.

The synthetic route of 75024-22-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Maiereanu, Carmen; Schmitt, Celine; Schifano-Faux, Nadge; Le Nouen, Didier; Defoin, Albert; Tarnus, Celine; Bioorganic and Medicinal Chemistry; vol. 19; 18; (2011); p. 5716 – 5733;,
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. 7766-50-9, name is 11-Bromo-1-undecene, A new synthetic method of this compound is introduced below., Computed Properties of C11H21Br

[0129] 86 mmol of 1 1 -bromo1 -undecene and 91 mmol of triethoxy silane were added to a single neck RBF attached with an attached reflux condenser. Then 1.0 mL Karstedt’s catalyst (2 Wt. % solution in toluene, 0.1 mmol)) was added via syringe and flask was in the oil bath between 70 C for 2h. 1H NMR of the crude mixture showed a complete consumption of chain end olefin groups, however, a close examination of the spectrum showed presence of -15-20% olefin rearrangement products. Separation of (1 1 – bromoundecyl) triethoxysilane from rearrangement olefin and excess triethoxy silane was achieved by fractional distillation under high vacuum (Yield 67%).

The synthetic route of 7766-50-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; BOBADE, Sachin; POLISHCHUK, Orest; PADMANABAN, Munirathna; BASKARAN, Durairaj; (65 pag.)WO2019/81450; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 67567-26-4, 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. 67567-26-4 name is 4-Bromo-2,6-difluoroaniline, 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.

CuCl2 (0.77 g, 5.77 mmol) was dissolved in 200 mL of water. SOCl2 (29 mL, 0.40 mol) was added thereto at0C, and the mixture was stirred at room temperature for 18 hours. 4-bromo-2,6-difluoroaniline (20 g, 0.096 mol) wasdissolved in 240 mL of HCl and 900 mL of water, and the solution in which NaNO2 (7 g, 0.10 mol) was dissolved in 200mL of water was added thereto at 0C. The above thionyl chloride solution was added thereto, and the reaction wascarried out at room temperature for 1 hour to obtain the title compound (24 g, 85 %) in a solid form.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,6-difluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; LG Chem, Ltd.; KIM, Young Kwan; PARK, Sang Yun; JOO, Hyun Woo; CHOI, Eun Sil; PAEK, Seung Yup; KANG, Seung Wan; KIM, Byung Gyu; LEE, Chang Seok; KIM, Sung Wook; LEE, Sang Dae; (369 pag.)EP3239143; (2017); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1435-52-5, 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 1435-52-5 as follows.

In an oven-dried 100 mL round bottom flask boronic acid 3(1.00 g, 1.0 eq.) was added, followed by dibromobenzene 2 (3.60 g, 2.0 eq) and palladium reagent (150 mg) were dissolved in dioxane to give a yellow solution. Sodium bicarbonate aqueous solution (2 M, 14 mL) was added causing a beige suspension to form. The suspension was heated at 80 0C for 20 h. The reaction was evaporated to dryness and the residue partitioned between EtOAc (75 mL) and water (25 mL). The layers were separated and the organic layer washed with brine, dried over magnesium sulfate, filtered and evaporated to a yellow oil. The oil was chromatographed with hexanes to yield 1.07 g (57percent yield) of 4 as a white solid and 528 mg (30percent yield) of 5 as a white solid.

According to the analysis of related databases, 1435-52-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INFINITY DISCOVERY, INC.; WO2008/63300; (2008); A2;,
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 82842-52-2 as follows. Quality Control of 3-Bromo-2,4,6-trimethylaniline

EXAMPLE 207 ‘N-(2,2′,4,6,6′-Pentamethyl-1,1’-biphenyl-3-yl)-3-[(phenylsulfonyl)amino]thiophene-2-carboxamide Step One: To a solution of 3-bromo-2,4,6-trimethylaniline (1.07 g, 5.0 mmol) and 2,6-dimethylphenyl boronic acid (1.5 g, 10 mmol) in toluene (10 mL) was added potassium phosphate, tribasic (3.2 g, 15 mmol) and the resulting mixture was deoxygenated by passing a stream of nitrogen for approximately 10 minutes. 2-Dicyclohexylphosphino-2,6-dimethoxy-1,1’biphenyl (0.164 g, 0.4 mmol) and tris(dibenzylidineacetone)dipalladium(0) (92 mg, 0.1 mmol) were added together in one portion, and nitrogen bubbling continued for approximately 2 minutes. The mixture was then heated in an oil bath at 110 C. under nitrogen overnight. The mixture was cooled, concentrated and passed through a pad of course silica gel. The resulting residue was purified on silica using 14:1 to hexanes to ethyl acetate. The residue from this operation was then vacuum distilled (Kugelrohr, 100 C., approximately 1 mtorr) to give the desired biphenyl (155 mg).

According to the analysis of related databases, 82842-52-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wu, Chengde; Anderson, C. Eric; Bui, Huong; Gao, Daxin; Kassir, Jamal; Li, Wen; Wang, Junmei; Biediger, Ronald; Chen, Jie; Market, Robert V.; US2005/49286; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

3814-30-0, name is (Bromomethyl)cyclopentane, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of (Bromomethyl)cyclopentane

General procedure: Potassium carbonate (791 mg, 5.7 mmol) was added to a solution of 3-iodoindazole (700 mg, 2.9 mmol) and 2-chloroethyl methyl ether (406 mg, 4.3 mmol) in ACN (20 mL) at rt. The reaction was heated to reflux overnight, and then was filtered and concentrated. The residue was purified by silica gel chromatography (15%-50% EtOAc/hexanes) to give 530 mg (63%) of the title compound as a light yellow oil. The title compounds were prepared from 5-fluoro-3-iodo-indazole and (bromomethyl)cyclopentane according to the procedure for Preparation 10A. [0365] 1-(cyclopentylmethyl)-5-fluoro-3-iodo-1H-indazole (72%) was isolated as the major isomer eluting first. 1H NMR (400 MHz, CDCl3): delta 1.25-1.32 (2H, m), 1.50-1.65 (6H, m), 2.48-2.56 (1H, m), 4.27 (2H, d, J=7.5 Hz), 7.09 (1H, dd, J=8.3, 2.3 Hz), 7.18 (1H, td, J=8.9, 2.4 Hz), 7.32 (1H, dd, J=9.1, 4.0 Hz). [M+H] calc’d for C13H14FIN2, 345. found 345. [0366] 2-(cyclopentylmethyl)-5-fluoro-3-iodo-2H-indazole (18%) was isolated as the minor isomer eluting second. 1H NMR (400 MHz, CDCl3): delta 1.33-1.42 (2H, m), 1.56-1.73 (6H, m), 2.62-2.70 (1H, m), 4.41 (2H, d, J=7.6 Hz), 7.00 (1H, dd, J=8.8, 2.4 Hz), 7.09 (1H, td, J=9.2, 2.4 Hz), 7.65 (1H, dd, J=9.3, 4.5 Hz). [M+H] calc’d for C13H14FIN2, 345. found 345.

The synthetic route of 3814-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Quanticel Pharmaceuticals, Inc.; Kanouni, Toufike; Stafford, Jeffrey Alan; Veal, James Marvin; Wallace, Michael Brennen; US2014/171432; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 138526-69-9, A common heterocyclic compound, 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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.

To a solution of 100 g of this 2-iodo-7-propyl-9,10-dihydrophenanthrene in 300 mL of THF was added 3.3 g of tetrakis(triphenylphosphine)palladium (0) and the mixture was stirred at room temperature. This mixture was then reacted with a Grignard reagent prepared from 79 g of 3,4,5-trifluorobromobenzene and 9.1 g of magnesium. Following stirring for 2 hours at room temperature, the mixture was allowed to cool to room temperature, water was added, the product was extracted into toluene, and the organic layer was washed sequentially with water and a saturated aqueous solution of sodium chloride before being dried over anhydrous sodium sulfate. The crude product obtained by removal of the solvent by evaporation was purified by silica gel columnchromatography (hexane) and then recrystallized 3 times from ethanol to yield 45 g of white crystals of 2-propyl-7-(3,4,5-trifluorophenyl)-9,10-dihydrophenanthrene. Measurement of the phase transition temperature revealed a transition from the crystalline phase to an isotropic liquid phase at 68C under rising temperature conditions. NMR: delta = 0.99 (t, J=7Hz, 3H), delta = 1.65 (m, 2H), delta = 2.52 (t, J=7Hz, 2H), delta = 2.88 (s, 4H), delta = 6.9 to 7.6 (m, 8H), MS: m/e = 352 (M+)

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; DAINIPPON INK AND CHEMICALS, INC.; EP1201632; (2002); A1;,
Bromide – Wikipedia,
bromide – Wiktionary