Tag: M.W=100-200

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. 1647-26-3.

Example 12: N-trans-(2-cyclohexylethyl)-2-phenylcyclopropanamine hydrochloride; To a solution Intermediate B (1.5g, 6.42 mmol) in Dimethylformamide (DMF, 30 mL) was added sodium hydride (0.38 mg, 9.64 mmol) and the suspension was stirred 30 min at room temperature. 1 -Cyclohexylethyl bromide (1.2 mL, 7.71 mmol) was then added and the suspension stirred 12h at room temperature. Solvents were evaporated and the residue was dissolved in dichloromethane (60 mL) and washed with water, brine and water, dried and concentrated. The obtained solid was purified by column chromatography to afford the Boc-protected product (1.4 g). This solid was dissolved in dichloromethane and HC1 (15 mL) was added. The precipitate was filtered, washed with cold ether and dried to afford the desired product (1.56 g, 88%). -NMR (CDC13) delta (ppm): 1.05 (m, 13H), 1 .2 1 (m, 1 H), 1 .44 (m, 1 H), 2.41 (m, 1 H), 2.92 (m, 1 H), 3.20 (m, 2H), 7.16-7.25 (m, 5H), 8.2 (bs, 2H). MS (M+H): 245.0.

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

Reference:
Patent; ORYZON GENOMICS S.A.; ORTEGA MUNOZ, Alberto; CASTRO-PALOMINO LARIA, Julio; FYFE, Matthew Colin Thor; WO2011/131697; (2011); A1;,
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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 2695-47-8 as follows. 2695-47-8

Sodium hydride (60% dispersion in mineral oil, 31.5 g, 1.28 eq.) was slowly added under nitrogen atmosphere to a solution of Lambda/-methyl-2,2,2-trifluoroacetamide (100 g, 1.28 eq.) in DMF (500 mL) at 0 0C. The reaction mixture was stirred for 90 min at 0 0C, and then 6-bromo-l-hexene (100 g, 1 eq.) was added dropwise over 45 min. The reaction mixture was allowed to warm up to room temperature, and stirred for 3 days at room temperature. The reaction mixture was then poured into water and extracted tree time with EtOAc. The combined organics layers were dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to produce compound 31A as colorless oil in 56% yield. 1U NMR (DMSO-J6, 400 MHz) delta 1.27-1.38 (m, 2H), 1.48-1.60 (m, 2H), 2.00-2.06 (m, 2H), 2.93-3.07(2m, 3H), 3.35-3.40 (m, 2H), 4.92- 5.04 (m, 2H), 5.73-5.83 (m, IH).

According to the analysis of related databases, 2695-47-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IDENIX PHARMACEUTICALS, INC.; PARSY, Christophe Claude; ALEXANDRE, Francois-Rene; LEROY, Frederic; CONVARD, Thierry; SURLERAUX, Dominique; WO2011/17389; (2011); A1;,
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The chemical industry reduces the impact on the environment during synthesis 39478-78-9, name is 5-Bromo-2-methylaniline, I believe this compound will play a more active role in future production and life. 39478-78-9

The compound 5-bromo-2-methylaniline (3.0g, 16.1mmol),Alpha-bromocyclopropanone (2.9 g, 17.7 mmol) and N,N-diisopropylethylamine (4.2 g, 32.2 mmol) were dissolved in 100 ml of toluene and reacted at 100C for 15 hours.After the reaction is over, the reaction solution is concentrated,The residue was subjected to silica gel column chromatography (ethyl acetate: petroleum ether = 1:30) to obtain 3.37g of product,The yield was 78.4%.

The chemical industry reduces the impact on the environment during synthesis 39478-78-9. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shandong Xuanzhu Pharmaceutical Technology Co., Ltd.; Wang Tingzhong; Liu Bin; (33 pag.)CN111170995; (2020); A;,
Bromide – Wikipedia,
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Some common heterocyclic compound, 5433-01-2, name is 1-Bromo-3-isopropylbenzene, molecular formula is C9H11Br, 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. 5433-01-2

Intermediate C. Method A: 3-Isopropylbenzoic acid (C-a). To a solution of l-bromo-3-isopropylbenzene (1.24 g, 6.23 mmol) in THF (18 ml) was added magnesium wire (0.151 g, 1 eq.). The mixture was heated to 50 to 600C until the magnesium was dissolved. To this solution was added an excess of solid CO2 and after 40 min the reaction mixture was acidified with IM aq. HCl. The product was extracted into DCM, the organic layer was dried over MgSO4 and evaporated, yielding the target product (1.07 g (quantitative)). 1H-NMR (CDCl3) delta (ppm) 8.00 (s, IH), 7.95 (d, IH), 7.49 (d, IH), 7.41 (t, IH), 3.00 (m, IH), 1.30 (d, 6H).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3-isopropylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; KEMIA, INC.; WO2007/75896; (2007); A2;,
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3814-30-0, 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. 3814-30-0, name is (Bromomethyl)cyclopentane, A new synthetic method of this compound is introduced below.

Example 19A Di-tert-butyl-{2-[5-(cyclopentylmethoxy)-1-benzofur-2-yl]-2-oxoethyl}[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]malonate To a mixture of 750 mg (1.33 mmol) of the compound from Example 7A and 552 mg (3.99 mmol) of potassium carbonate in 10 ml

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; BAYER PHARMA AKTIENGESELLSCHAFT; BECK, Hartmut; LI, Volkhart Min-Jian; CANCHO GRANDE, Yolanda; TIMMERMAN, Andreas; BROHM, Dirk; JOeRIssEN, Hannah; BOGNER, Pamel

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. 583-70-0, name is 2,4-Dimethylbromobenzene, A new synthetic method of this compound is introduced below., 583-70-0

To a solution of magnesium (1.17 g, 48.0 mmol) and lithium chloride (2.20 g, 60.0 mmol) in THF (40 ml) at room temperature was added 1 -bromo-2,4-dimethylbenzene (5.4 mE, 40.0 mmol) and the reaction was heated gently to reflux with a heat gun. The reaction was cooled to room temperature over 1 hr. The reaction was then cooled to 0 C., and Fe(acac)3 (0.71 g, 2.00 mmol) dissolved inS mE of THF was added. After 5 minutes, allyl chloride (4.23 mE, 52.0mmol) was added and the reaction was stirred at 0 C. for 30 mm. The mixture was warmed to room temperature over 1 hr and was heated at 70 C. overnight. The reaction was cooled to 0 C. and quenched by the addition of a saturated NaHCO3 solution (50 mE). The mixture was extracted with hexane (3×40 mE), the combined organic phases were washed with brine (50 mE), dried over Na2 SO4 and carefully concentrated (25 C., 250 mbar). The residue was purified by Isco chromatography (100% hexane as the eluent) to provide i-allyl-2,4-dimethylbenzene (2.75 g, 15.04 mmol, 38% yield) as a colorless oil. ?H NMR (400 MHz, CDC13) oe 7.11-6.87 (m, 3H), 5.93 (ddt, J=i6.6, 10.1, 6.4 Hz, iH), 5.19-4.85 (m, 2H), 3.33 (dd, J=6.4, 1.5 Hz, 2H), 2.29 (s, 3H),2.25 (s, 3H).

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; Dow AgroSciences LLC; Loy, Brian A.; Rigoli, Jared W.; Sam, Brannon; Meyer, Kevin G.; Yao, Chenglin; (32 pag.)US2018/186743; (2018); A1;,
Bromide – Wikipedia,
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55289-36-6, These common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-methylaniline, 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.

Reference Example 19; 4-Bromo-2-trifluoromethyl-lJH-indoIe; A solution of 2-methyl-3-bromo-aniline (6.05 g, 37 mmol) in pyridine (8 mL) and DCM (150 mL) was cooled to 0 C and treated drop-wise with trifluoroacetic anhydride (11.5 mL, 81.4 mmol). The reaction mixture was stirred at RT for 2 h, then quenched with an aqueous solution of ammonium chloride. The organic layer was dried over MgSO4, and evaporated to dryness to give N-(3-bromo-2-methyl-phenyl)-2,2,2-trifluoro-acetamide as an off-white solid, which was used without further purification (10 g).NMR deltaH (400 MHz, CDCl3) 2.38 (s, 3H), 7.14 (apparent t, J = 8.0, IH), 7.53 (d, J = 8.0, IH),7.66 (d, J = 8.0, IH) and 7.75 (bs, IH).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 55289-36-6.

Reference:
Patent; PIRAMED LIMITED; THE INSTITUTE OF CANCER RESEARCH; WO2008/125835; (2008); A1;,
Bromide – Wikipedia,
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2695-48-9, 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 2695-48-9 as follows.

(III) 4-(7-octeneoxy) benzoic acid 8-Bromo-1-octene (23.9 g, 0.125 mole), ethyl 4-hydroxybenzoate (18.28 g, 0.11 mole) and 18-crown-6 (1.35 g, 0.0055 mole) are dissolved in 150 ml of acetone in a 500 ml round-bottomed flask. Potassium carbonate (45.6 g, 0.33 mole) is added to the flask and the resulting mixture is stirred and refluxed for 24 hr. The mixture is filtered to remove the salts and the filtrate is evaporated under reduced pressure to yield a light yellow oil. 200 ml of 2M KOH is added to the oil and the resulting mixture is stirred and refluxed for five hours. The resulting clear yellow solution is cooled to room temperature and acidified with HCl. The resulting white precipitate is filtered off, washed with water, recrystallized from 125 ml of ethanol and dried under vacuum. Yield, 23.4 g (86% based on ethyl 4-hydroxybenzoate).

According to the analysis of related databases, 2695-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Aerospace Corporation; US5237076; (1993); A;,
Bromide – Wikipedia,
bromide – Wiktionary

55289-36-6, A common compound: 55289-36-6, name is 3-Bromo-2-methylaniline, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

A mixture of 3-bromo-2-methylaniline (4.000g) , 4, 4, 4′, 4′, 5, 5, 5′, 5′-octamethyl-2, 2′-bi (1, 3, 2-dioxaborolane) (6.550g) and potassium acetate (4.220g) in 1, 4-dioxane (44.8mL) and DMSO (9.0mL) was purged with nitrogen for 10 min. [1, 1′-Bis (diphenylphosphino) ferrocene] -dichloropalladium DCM adduct (0.527g) was added, the mixture was purged for another 5min then was heated at reflux for 2h. The mixture was cooled and filtered through Celite. The solids were washed with EtOAc, and the combined filtrates were washed with water and brine, and dried and concentrated. The residue was purified by column chromatography (eluting with hexane-EtOAc using a gradient from 20: 1 to 85: 15) . 2-methyl-3- (4, 4, 5, 5-tetramethyl- 1, 3, 2-dioxaborolan-2-yl) aniline (compound M1) as a light yellow waxy solid (4.400g, 88%) .[0356]1H NMR (400 MHz, chloroform-d) delta 7.21 (1H, dd, J=7.3, 1.0 Hz) , 7.02 (1H, t, J=7.7 Hz) , 6.75 (1H, dd, J=7.8, 1.0 Hz) , 3.54 (2H, br. s. ) , 2.37 (3H, s) , 1.34 (12H, s) . Mass spectrum m/z 233.3, 234.3, 235.3 (M+H)+.

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, 3-Bromo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BETTA PHARMACEUTICALS CO., LTD; WANG, Yiqian; FU, Bang; ZHANG, Yao; LIU, Xiangyong; WANG, Jiabing; DING, Lieming; (103 pag.)WO2019/192506; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

553-94-6, These common heterocyclic compound, 553-94-6, name is 2,5-Dimethylbromobenzene, 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: In the first step,reference solution (CPd=0.5¡Á10-4mmol/mL,CLigand=1.0¡Á10-4mmol/mL) was prepared. A single-neckedground tube (rinner=1.1 cm, L=17.5 cm) was equipped with a magnetic stirbar. 0.5 mmol of aryl halides, 0.75 mmol of phenyl boronic acid and 1 mmol basewere added into the tube under atmospheric condition. Then, appropriate amountof reference solution and solventwere added into the tube. The reaction mixture was stirredat the pre-arranged temperature for appropriate reaction time in oil bath. Afterthe reaction was completed, 3 mL water was added, and the mixture was extractedwith EtOAc(10 mL¡Á4). Then the organic phase was dried with Na2SO4and concentrated under reduced pressure. The residue was then purified by columnchromatography on silica gel. The pure product was obtained and was analyzed by1H NMR spectroscopy.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 553-94-6.

Reference:
Article; Liu, Haiyang; Liu, Hailong; Li, Ruixiang; Chen, Hua; Tetrahedron Letters; vol. 55; 2; (2014); p. 415 – 418;,
Bromide – Wikipedia,
bromide – Wiktionary