Month: November 2020

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. 5433-01-2, name is 1-Bromo-3-isopropylbenzene, A new synthetic method of this compound is introduced below., 5433-01-2

A mixture of N- (4- (methylsulfonyl ) benzyl) -3, 4-dihydro-2H- 1 , 4-benzoxazine-7-carboxamide (0.028 g, 0.08 mmol), l-bromo-3- isopropylbenzene (32 mg, 0.160 mmol), RuPhos Pd Gl (5.83 mg, 8.00 mumol), RuPhos (3.73 mg, 8.00 mumol), NaOtBu (0.023 g, 0.240 mmol) and DME (1 mL) was heated at 130 C for 2 h under (3792) microwave irradiation. The reaction mixture was diluted with AcOEt (3 mL) and quenched with H2O (1 mL) , and stirred for 2 min. The organic layer was separated and then the aqueous layer was extracted with EtOAc (2 mL) . The combined organic layer was evaporated by blowing away with the air at 60 C. The residue was purified by preparative HPLC (Actus Triart C18, eluted with MeCN/10 mM NH4HCO3 aq. 5 : 95?100 :?0 ) . Pure fractions were combined and concentrated by blowing away with the air at 60C to afford the title compound (21.9 mg, 0.0471 mmol, 59%) .

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; YAMAMOTO, Satoshi; SHIRAI, Junya; KONO, Mitsunori; SHIOKAWA, Zenyu; YUKAWA, Tomoya; IMADA, Takashi; NEGORO, Nobuyuki; ODA, Tsuneo; SASAKI, Satoshi; NARA, Yoshi; SUZUKI, Shinkichi; SATO, Ayumu; ISHII, Naoki; SHIBUYA, Akito; NAKAGAWA, Yasuo; COLE, Derek; GIBSON, Tony; IVETAC, Anthony; SWANN, Steve; TYHONAS, John; (472 pag.)WO2018/30550; (2018); A1;,
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. 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., 38573-88-5

To a solution of 1-bromo-2,3-difluorobenzene (2.48 g, 12.86 mmol) in dry diethylether (40 ml) at -78¡ã C. was added dropwise n-butyllithium (2.5 M in hexane, 5.1 ml, 12.86 mmol). The mixture was stirred for 30 min after which a solution of 1-Boc-azetidone (2.0 g, 11.69 mmol) in dry diethyl ether (20 mL) was added dropwise. The resulting mixture was stirred at -78¡ã C. for 30 min and then brought to ambient temperature and stirred for 1 h. Aqueous saturated ammonium chloride (50 mL) was added and the mixture was extracted with ethyl acetate (2.x.50 ml). The combined organic phase was dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (ethylacetate/isooctane 1:1) to give the title compound Yield: 1.89 g. MS m/z (rel. intensity, 70 eV) 285 (M+, 1), 156 (68), 141 (40), 127 (63), 57 (bp).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; NSAB, FILIAL AF NEUROSEARCH SWEDEN AB, SVERIGE; US2011/257148; (2011); 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

454-65-9, 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 454-65-9 as follows.

To a stirred solution of 3-BROMOPHENYLSULFONYL fluoride (D1) (1 g, 4.18 MMOL) in dry THF (20 ml) at-78 C, under argon was added phenylmagnesium bromide (1 M, 1.4 ML, 4.18 MMOL) dropwise. The reaction was left to warm to room temperature overnight and then quenched with ammonium chloride (50 ml), extracted with ethyl acetate (3 X 40 mi) and the combined organic extracts dried (NA2SO4). SOLVENTS WERE EVAPORATED IN VACUO to give A colourless solid (1.09 g, 88 %). 1H NMR (CDCl3) : No. 7.40 (1H, t), 7.50-7. 55 (2H, m), 7.60 (1H, d), 7.69 (1H, d), 7. 86 (1H, d), 7.93 (2H, d), 8. 08 (1H, s).

According to the analysis of related databases, 3-Bromobenzene-1-sulfonyl fluoride, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/80986; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 16518-62-0 name is 3-Bromo-N,N-dimethylaniline, 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. 16518-62-0

N,N-dially-3-bromobenzene amine (10.0 g, 39.8 mmol) and N,N-dimethyl-3-bromobenzene amine (2.73 g, 13.6 mmol) were dissolved in acetic acid (150 mL), a 37percent formaldehyde solution (10.9 g, 363 mmol) was added, and the system was heated for 60 minutes at 80¡ãC. The system was cooled to room temperature and subsequently neutralized with a saturated aqueous solution of NaOH, and the precipitates were dissolved in H2O. The resulting mixture was extracted using dichloromethane and washed using a saline solution. The organic layer was dried using Na2SO4, the solvent was removed, and the residue was thereafter refined using column chromatography (silica gel, 1/30 ethyl acetate/hexane) to obtain 4-(2-bromo-4-(dimethylamino)benzyl)-N,N-diallyl-3-bromobenzene amine (3.67 g, 7.91 mmol, yield: 58percent).1H-NMR (300.40 MHz, CDCl3) : delta2.93 (s, 6H), 3.87 (d, 4H, J = 4.2 Hz), 3.98 (s, 2H), 5.13-5.19 (m, 4H), 5.73-5.88 (m, 2H), 6.53 (dd, 1H, J = 1.5 Hz, 8.7 Hz), 6.58 (dd, 1H, J = 1.5 Hz, 8.7 Hz), 6.79 (d, 1H, J = 9.0 Hz), 6.86 (d, 1H, J = 8.7 Hz), 6.90 (d, 1H, J = 1.5 Hz), 6.93 (d, 1H, J = 1.5 Hz). 13C-NMR (75.45 MHz, CDCl3): delta39.8, 40.5, 52.7, 111.7, 111.8, 116.0, 116.2, 125.5, 125.6, 126.9, 127.1, 130.7, 130.8, 133.5, 148.1, 150.0LRMS (ESI+): 465 for [M+H]+

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

Reference:
Patent; The University of Tokyo; NAGANO Tetsuo; HANAOKA Kenjiro; EGAWA Takahiro; KUSHIDA Yu; NUMASAWA Koji; MYOCHIN Takuya; PIAO Wen; EP2942352; (2015); A1;,
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

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, 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,
bromide – Wiktionary

699-03-6, 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. 699-03-6, name is 1-(4-Bromophenyl)-N-methylmethanamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of (S)-2-{(4-morpholin-4-yl-benzyl)-[3-(6-trifluoromethyl-pyridin-3-yl)-acryloyl]- amino}-3-phenyl-propionic acid (4.00 g, 7.41 mmol), TBTU (4.76 g, 14.83 mmol), and cat. DMAP in dry DCM (45 ml.) was added DIPEA (3.8 ml_, 22.24 mmol). The resulting mixture was stirred at rt for 10 min and then (4-bromo-benzyl)-methyl-amine (1.48 g, 7.41 mmol) was added. The reaction mixture was stirred at rt overnight under nitrogen atmosphere, then concentrated in vacuo. The resulting residue was taken up in EA. The organic layer was washed with water (5x) and brine, dried (MgSO4), filtered and concentrated under reduced pressure. FC (n-heptane/EA 5:5) afforded the N-{1-[(4-bromo-benzyl)-methyl- carbamoyl]-2-phenyl-ethyl}-N-(4-morpholin-4-yl-benzyl)-3-(6-trifluoromethyl-pyridin-3-yl)- acrylamide as a yellow foam (2.38 g, 44%).LC-MS (analytic A, Zorbax SB-AQ column, acidic conditions): tR = 1.16 min; [M+H]+ = 722.76

The synthetic route of 1-(4-Bromophenyl)-N-methylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; AISSAOUI, Hamed; BOSS, Christoph; CORMINBOEUF, Olivier; FRANTZ, Marie-Celine; GRISOSTOMI, Corinna; WO2010/58353; (2010); 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. 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,
bromide – Wiktionary