Author: Jessica.F

Synthetic Route of 201849-17-4, These common heterocyclic compound, 201849-17-4, name is 1-Bromo-2-chloro-5-fluoro-4-methylbenzene, 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 solution of isopropyl magnesium chloride in THF (2.0 M; 27.2 mL) was added dropwise to a mixture of 1-bromo-2-chloro-5-fluoro-4-methylbenzene (8.10 g) and THF (55 mL) at -10 C. under an argon atmosphere, followed by stirring at -10 C. for 45 minutes. A mixture of iodine (18.4 g) and THF (26 mL) was added dropwise to the reaction mixture at -75 C., followed by stirring at -75 C. for 3 hours. A saturated aqueous Na2S2O3 solution was added to the reaction mixture at -75 C., followed by stirring at room temperature for 15 minutes. Saturated aqueous sodium bicarbonate was added to the reaction mixture at room temperature, followed by extraction with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and then concentrated under reduced pressure, thereby obtaining 1-chloro-4-fluoro-2-iodo-5-methylbenzene (9.71 g).

Statistics shows that 1-Bromo-2-chloro-5-fluoro-4-methylbenzene is playing an increasingly important role. we look forward to future research findings about 201849-17-4.

Reference:
Patent; ASTELLAS PHARMA INC.; ISHIHARA, Tsukasa; IKEGAI, Kazuhiro; KURIWAKI, Ikumi; HISAMICHI, Hiroyuki; TAKESHITA, Nobuaki; TAKEZAWA, Ryuichi; US2014/364421; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2687-12-9, name is Cinnamyl chloride, belongs to chlorides-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 2687-12-9, Quality Control of Cinnamyl chloride

To a suspension of 500 mg (1.99 mmol) of Example 11 Part A compound in 10 mL of THF, at 0C under argon, was added dropwise 2.5 mL (3.98 mmol) of n-BuLi (1.6 M in hexanes). The resulting orange solution was stirred at 0C for 0.5 h at which time 305 muL (2.19 mmol) of cinnamyl chloride was added. The reaction was warmed to RT and allowed to stir for 1 h at which time it was diluted with 1:1 ethyl acetate/water (30 mL). The organics were dried (NaSO4) and evaporated to dryness. Purification by crystallization from hot methanol provided 350 mg (48%) of title compound as a white solid. mp 95-97C. TLC Silica gel (1:1 hexanes/ethyl acetate) Rf = 0.59. MS (CI-NH3, + ions) m/e 368 (M+H).

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; BRISTOL-MYERS SQUIBB COMPANY; EP904262; (2004); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 14862-52-3, 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 14862-52-3 as follows.

1,3-dibromo-5-chlorobenzene (100 g, 370 mmol) was dissolved in THF (2 L) in a nitrogen environment, phenylboronic acid (47.3 g, 388 mmol) and tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (1.5 g, 1.36 mmol) were added thereto, and the mixture was stirred. Potassium carbonate (K2CO3) (127 g, 925 mmol) saturated in water was added thereto, and the resulting mixture was heated and refluxed at 80 C. for 12 hours. When the reaction was complete, water was added to the reaction solution, the mixture was extracted with dichloromethane (DCM), and an extract therefrom was filtered and concentrated under a reduced pressure after removing moisture with anhydrous MgSO4. The obtained residue was separated and purified through flash column chromatography to obtain an intermediate I-6 (49 g, 50%). HRMS (70 eV, EI+): m/z calcd for C12H8BrCl: 265.9498, found 266 Elemental Analysis: C, 54%; H, 3%

According to the analysis of related databases, 14862-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAMSUNG SDI CO., LTD.; KANG, Giwook; KIM, Younhwan; KIM, Youngkwon; KIM, Dongyeong; KIM, Hun; OH, Jaejin; CHO, Pyeongseok; YU, Eun Sun; (176 pag.)US2017/92873; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 2845-89-8, name is 1-Chloro-3-methoxybenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 2845-89-8

General procedure: Under an N2atmosphere, KOtBu (1.3 mmol), complex 1 (1 mol%),dioxane (2 ml), amines (1.3 mmol) and aryl chlorides (1.0 mmol)were successively added into a Schlenk tube. The mixture wasstirred vigorously at 90C for 4 h. Then the solvent was removedunder reduced pressure and the residue was purified by columnchromatography on silica gel (eluent:PE/EA = 15:1) to give the pureproducts. The reported yields are the average of two runs.The catalytic reactions have been given in Tables 4-7. The result-ing amines were identified by comparison of the1H and13C NMRdata with those previously reported (ESI).

The synthetic route of 2845-89-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nirmala, Muthukumaran; Prakash, Govindan; Ramachandran, Rangasamy; Viswanathamurthi, Periasamy; Malecki, Jan Grzegorz; Linert, Wolfgang; Journal of Molecular Catalysis A: Chemical; vol. 397; (2015); p. 56 – 67;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 108-41-8,Some common heterocyclic compound, 108-41-8, name is 1-Chloro-3-methylbenzene, molecular formula is C7H7Cl, 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: To a 50 mL Schlenk tube containing base (1.5 mmol) and precatalyst 4a (1 mol %, 0.0083 g) purged with N2 (three times), amine (1.2 mmol) was added via syringe, and the resulted mixture was allowed to stir at room temperature for 2-3 min. Solvent (1 mL) was then injected via syringe followed by the aryl chloride (1.0 mmol). If the aryl chloride was a solid, it was introduced into the vial prior to purging with N2. At this time, the reaction was stirred for 24 h at 100 C. After cooling to the room temperature, the reaction mixture was concentrated in vacuo and directly purified via silica gel flash chromatography. 4-(m-tolyl)morpholine (7b) ;1H NMR (CDCl3, 400 MHz, 298 K): delta=7.22 (t, J=7.2 Hz, 1H), 6.79-6.77 (m, 3H), 3.89 (m, 4H), 3.18 (m, 4H), 2.38 (s, 3H); 13C NMR (CDCl3, 100 MHz, 298 K): delta=151.22, 138.68, 128.87, 120.80, 116.38, 112.72, 66.81, 49.30, 21.64.

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

Reference:
Article; Fang, Weiwei; Jiang, Jian; Xu, Yong; Zhou, Juefei; Tu, Tao; Tetrahedron; vol. 69; 2; (2013); p. 673 – 679;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 20850-43-5 as follows. HPLC of Formula: C8H7ClO2

General procedure: Suspension of the appropriate 3-amino-1,1-dioxo-1,4,2-benzodithiazine derivative 4a-h (0.5 mmol), anhydrous K2CO3 (1.5 mmol, 0.21 g) and the appropriate alkyl chloride (0.6 mmol) in dry THF (5 ml) was heated at reflux for 20-24 h, then cooled in ice-bath and filtered off. The crude product was suspended in 5 ml of water, heated gently to ca. 50 C; and cooled with vigorous stirring until granular precipitate appeared. Filtering off and washing with cold water and diluted EtOH gave pure potassium salts. 4.5.11 ;N-{2-[(1,3-Benzodioxol-5-yl)methylthio]-4-chloro-5-(3-phenyl-1,2,4-oxadiazol-5-yl)benzenesulfonyl}cyanamide potassium salt (5o) ;Starting from 4g (0.196 g) and 1,3-benzodioxol-5-ylmethyl chloride (0.102 g). Yield: 0.215 g (88%): m.p. 274-276 C; IR (KBr): nu 2923, 2179, 1625, 1585, 1560, 1500, 1488, 1362, 1349, 1253, 1226, 1143 cm-1; 1H NMR (500 MHz, DMSO-d6): delta 4.38 (s, 2H, SCH2), 6,01 (s, 2H, OCH2O), 6.90 (d, J = 7.81 Hz, 1H, Ar), 6.98 (d, J = 7.81 Hz, 1H, Ar), 7.05 (s, 1H, Ar), 7.59-7.63 (m, 3H, Ar), 7.70 (s, 1H, Ar), 8.10-8.11 (m, 2H, Ar), 8.59 (s, 1H, Ar); Anal. C23H14ClKN4O5S2 (C, H, N).

According to the analysis of related databases, 20850-43-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Brozewicz, Kamil; Slawinski, Jaroslaw; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 384 – 394;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

50638-47-6, name is 4-Bromo-2-chloro-1-methoxybenzene, belongs to chlorides-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. COA of Formula: C7H6BrClO

EXAMPLE 21 Preparation of 5-Hydroxy-3-(3-chloro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-cyclopent-2-en-1-one of Formula (67) [0134] A mixture of magnesium turnings (0.31 g, 13.1 mmol), 2-chloro-4-bromoanisole (3.00 g, 13.5 mmol), 4-tert-butyldimethysilyloxy-2-(3,4,5-trimethoxy-phenyl)-cyclopent-2-en-1-one (2.58 g, 6.84 mmol) and dry tetrahydrofuran (35 ml) under nitrogen was stirred at room temperature for 4 h. Reaction was then quenched with dil hydrochloric acid (30 ml), tetrahydrofuran was removed under reduced pressure and the residual reaction mixture was extracted with ethyl acetate (3*35 ml), washed with water (2*20 ml) and dried over sodium sulfate. Concentration and purification by column chromatography over silica gel (eluent-6% acetone in pet ether) afforded the alcohol of the formula (4A) [0135] wherein R1=R5=R6=R7=R10=H, R2=R3=R4=R8=OMe, R9=Cl (1.32 g, 37%). [0136] A solution of the above alcohol of the formula (4A) wherein R1=R5=R6 =R7=R10=H, R2=R3=R4=R8=OMe, R9=Cl wherein (0.95 g, 1.83 mmol) in dry dichloromethane (15 ml) was cooled to 0 C., pyridinium dichromate (1.92 g, 8.17 mmol) was added and the mixture was stirred at room temperature for 3 h. Filtration through celite (3.00 g), washing with dichloromethane (30 ml) and concentration afforded the crude product which was purified by silica gel column chromatography (eluent-3% acetone in pet ether) to yield the title compound of the formula (1B) wherein R=OTBS, R1=R5=R6=R7=R10=H, R2=R3=R4=R8=OMe, R9=Cl (0.32 g, 34%), which on deprotection of TBDMS group using the procedure described in example 10 furnished the compound of formula (67). [0137] Spectral data of compound of the formula of structure (67) [0138] 1H NMR(CDCl3+CCl4): delta 2.96 (dd, J=18 Hz and 2 Hz, 1H), 3.33 (dd, J =18 Hz and 6 Hz, 1H), 3.75 (s, 6H), 3.86 (s, 3H), 3.91 (s, 3H), 4.45-4.54 (m, 1H), 6.42 (s, 2H), 6.81 (d, J=8 Hz, 1H), 7.21-7.29 (m, 1H), 7.48 (bs, 1H). [0139] 13C-NMR (CDCl3+CCl4): delta 37.79, 55.87 (2C), 60.58, 71.57, 106.23 (2c), 111.31, 122.41, 126.82, 127.59, 128.58 (2C), 130.05, 135.90, 138.07, 153.36 (2C), 156.48, 162, 51, 206.95

The synthetic route of 50638-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DABUR RESEARCH FOUNDATION; WO2004/56738; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, belongs to chlorides-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 1996-30-1, Recommanded Product: 3-Bromo-4-fluorochlorobenzene

890 p1 (7.0 mmol) of 2-bromo-4-chloro-1-fluorobenzene, 720 mg (7.02 mmol) of 4-chloro-1H- imidazole, 2.91 g (21.1 mmol) of potassium carbonate and 30 ml DMF were divided into twomicrowave vessels and stirred in the microwave at 130C for 3 hours. After cooling, the two reaction mixtures were combined and 150 ml of cold water were added with stirring. This mixture was stirred for 5 mm. The suspension was then filtered and the solid was washed with ice-water and pentane and dried under high vacuum. Yield: 1.33 g (64% of theory)LC/MS [Method 1]: R = 0.97 mm; MS (ESIpos): m/z = 293 (M+H),?H-NMR (400 MHz, DMSO-d6): oe [ppm] = 8.05 (d, 1H), 7.89 (d, 1H), 7.68-7.59 (m, 3H).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; JIMENEZ NUNEZ, Eloisa; ACKERSTAFF, Jens; ROeHRIG, Susanne; HILLISCH, Alexander; MEIER, Katharina; HEITMEIER, Stefan; TERSTEEGEN, Adrian; STAMPFUSS, Jan; ELLERBROCK, Pascal; MEIBOM, Daniel; LANG, Dieter; (399 pag.)WO2017/5725; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, belongs to chlorides-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. HPLC of Formula: C4H6Cl2

General procedure: To a cooled solution (5 C) of the corresponding 4,6-O-(R)-benzylidene-d-hexopyranoside derivative (obtained using the procedure describe by our group2c) (35.4 mmol) in dry THF (70 mL) were added, successively, freshly powdered potassium hydroxide (7.0 g, 125 mmol), 18-crown-6 (0.38 g, 1.4 mmol), and 3-chloro-2-chloromethylpropene (4.1 mL, 35.4 mmol). The reaction mixture was stirred at this temperature for 3 h, and left at room temperature until all the starting material had been consumed, as monitored by TLC (5-7 days, approximately), then diluted with dichloromethane (60 mL) and washed successively with water and aqueous saturated solution of sodium bicarbonate, dried (MgSO4), filtered, and the filtrate was evaporated to dryness.

The synthetic route of 1871-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vega-Perez, Jose M.; Vega-Holm, Margarita; Perinan, Ignacio; Palo-Nieto, Carlos; Iglesias-Guerra, Fernando; Tetrahedron; vol. 67; 2; (2011); p. 364 – 372;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 918538-05-3, A common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, molecular formula is C6H3Cl2N3, 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.

1C. 2-Chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrrolo[1,2-f][1,2,4]triazin-4-amine A mixture of 1B (977 mg, 5.2 mmole), 5-cyclopropyl-1H-pyrazol-3-amine (640 mg, 1 equiv), and diisopropylethylamine (1.54 mL, 1.7 equiv) in isopropyl alcohol (5 mL) was stirred at RT overnight. The product was collected by filtration (1.18 gm, 83% yield): MS: 275 (M+H)+; HPLC Ret Time: 1.56 min.

The synthetic route of 918538-05-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/9497; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics