Month: May 2021

Reference of 1481-63-6, A common heterocyclic compound, 1481-63-6, name is 1-Bromo-2,4-dichloro-5-fluorobenzene, molecular formula is C6H2BrCl2F, 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.

EXAMPLE 5 65.4 ml of butyl acrylate, 450 mg of palladium acetate, 1.075 g of triphenylphosphane, 0.815 g of bis(phenylphosphino)ethane and 20.15 g of sodium acetate are added to 50.0 g of 1-bromo-2,4-dichloro-5-fluorobenzene under protecting gas and the mixture is dissolved in 100 ml of dimethylacetamide. The reaction mixture is boiled for 12 hours at 140-145 C. The mixture is then diluted with 200 ml of dichloromethane and washed twice by shaking with 100 ml of water. The organic phase is concentrated by a rotary evaporator. Yield: 86% of butyl 2,4-dichloro-5-fluorocinnamate.

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; Hoechst Aktiengesellschaft; US5516932; (1996); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 2162-98-3,Some common heterocyclic compound, 2162-98-3, name is 1,10-Dichlorodecane, molecular formula is C10H20Cl2, 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.

1,10-Dichlorodecane (8.73 g, 41.3 mmol) and triethylamine (6 mE) were added to a solution of m-aminophenol (3.85 g, 35.3 mmol) in DMF (40 mE). The mixture was stirred at 1000 C. for 3 days. The reaction was quenched with sam- 40 rated aqueous NaHCO3 and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, hexane_EtOAc=9:i to 1:1) to give the title compound (1.92 g, 6.76 mmol, 19% yield). Brown oil; R1=0.57 (33% EtOAc-hexane); ?H NMR (600 MHz, DM50- d5) oe 8.84 (s, 1H), 6.80 (dd, J=7.6, 8.3 Hz, 1H), 5.97 (d, J=7.6 Hz, 1H), 5.94 (s, 1H), 5.92 (d, J=8.2 Hz, 1H), 5.36 (s, 1H), 50 3.61 (m, 2H), 2.89 (m, 2H), 1.69 (m, 2H), 1.49 (m, 2H),1.35-1.25 (m, 12H); ?3C NMR (150 MHz, DMSO-d5) oe158.3, 150.6, 129.5, 103.7, 103.0,98.9,45.6,43.1,32.2,29.2,29.1 x2, 28.9,28.4,26.9,26.4; FABMS m/z 283 [M]; HRMS calcd. for C,6H26N0C1 [M] 283.1703. found 283.1708. 55theoil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,10-Dichlorodecane, its application will become more common.

Reference:
Patent; KYOTO UNIVERSITY; Uesugi, Motonari; Hirata, Nao; Murata, Asako; Chang, Young-Tae; Nakatsuji, Norio; Suemori, Hirofumi; Kawase, Eihachiro; Yamauchi, Kaori; Ueda, Kazumitsu; Fujibayashi, Yuto; Yamanaka, Shinya; Nakagawa, Masato; (34 pag.)US9335323; (2016); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 106246-33-7, 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 106246-33-7 as follows.

EXAMPLE 1a Production of 4,4′-methylene-bis-(3-chloro-2,6-diethylphenylisocyanate) 100 g (0.26 mmol) of 4,4′-methylene-bis-(3-chloro-2,6-diethylaniline) was introduced into 1000 g of dichlorobenzene in an autoclave at room temperature. 57 g (0.58 mol) of phosgene was introduced into this solution over a period of 30 minutes. The reaction mixture was stirred in a sealed autoclave at 80 C. for 1 hour. Then, it was depressurized, and the hydrochloric acid that was produced, the excess phosgene, and the solvent were removed. In this case, the title product resulted in a yield of 110 g (98% of theory). Other data concerning the product is: IR (KBr): 2288.1 cm-1 1 H-NMR (CDCl3, 400 MHz) in ppm: 6.69 s, 2H; 4.12 s, 2H; 2.91 q, 4H, J=7.5 Hz; 2.59 q, 4H, J=7.6 Hz; 1.20 t, 6H, J=7.6 Hz; 1.15 t, 6H, J=7.5 Hz.

According to the analysis of related databases, 106246-33-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lonza AG; US5734076; (1998); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16429-44-0, name is 5-Bromo-3-chlorobenzene-1,2-diamine, 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 16429-44-0, SDS of cas: 16429-44-0

5-bromo-7-chloro-1H-benzimidazole A solution of 5-bromo-3-chlorobenzene-1,2-diamine (2 g, 9.03 mmol) in formic acid (30 ml) was heated at reflux for 16 hours. The reaction progress was monitored by LCMS. Reaction mixture was concentrated under vacuum to yield brown oil. The mixture was extracted by EtOAc from a saturated aqueous solution of NaHCO3, dried over MgSO4 and evaporated under vacuum to yield 5-bromo-7-chloro-1H-benzo[d]imidazole as a pale yellow solid. Mass spectrum (EI, m/z): Calculated for C7H4BrClN2, 232.5 (M+H), found 233.0.

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, 5-Bromo-3-chlorobenzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Janssen Pharmaceutica NV; Zhang, Xuqing; Macielag, Mark J.; (179 pag.)US2019/47959; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 204930-37-0, 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. 204930-37-0, name is 5-Bromo-1,3-dichloro-2-methylbenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 10; 5-bromo-2-(bromomethyl)-l,3-dichlorobenzene; Heat to reflux a solution of 5-bromo-l,3-dichloro-2-methylbenzene (97 mg, 0.40 mmol), N-bromosuccinimide (76 mg, 0.425 mmol) and benzoyl peroxide (16 mg, 0.06 mmol) in CCl4 (5 mL) for 3 hours under N2. Cool the reaction to room temperature and concentrate to an orange residue. Purify the residue by silica gel chromatography eluting with hexanes to afford 112 mg (87percent) of the product as white crystals.

The synthetic route of 5-Bromo-1,3-dichloro-2-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WALLACE, Owen, Brendan; WO2007/127726; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 202925-05-1,Some common heterocyclic compound, 202925-05-1, name is 4-Chloro-3,5-dibromotoluene, molecular formula is C7H5Br2Cl, 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.

Example 7-10 4-[8-(4-Chloro-3,5-dicyclopropylbenzyl)-2-oxo-l-oxa-3,8-diazaspiro[4.5]dec-3-yl]benzoic acid, TFA saltStep 1. Synthesis of I,3-dibromo-5-(bromomethyI)-2~chlorobenzene To l,3-dibromo-2-chloro-5-methylbenzene (1000 mg, 3.52 mmol) was added NBS (688 mg, 3.87 mmol) and AIBN (57.7 mg, 0.352 mmol). The mixture was stirred at room temperature for 30 minutes and then heated to 80 C overnight. The solution was evaporated and the residue was purified by silica gel chromatography (0-5% EtOAc/heaxnes) to provide the title compound (740 mg) as a clear oil

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-3,5-dibromotoluene, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DUFFY, Joseph, L.; BAO, Jianming; ONDEYKA, Debra, L.; TYAGARAJAN, Sriram; SHAO, Patrick; YE, Feng; KATIPALLY, Revathi; ZWICKER, Aaron; SHERER, Edward, C.; PLOTKIN, Michael A.; MONINGKA, Remond; HUSSIAN, Zahid; WOOD, Harold B.; UJJAINWALLA, Feroze; ROMERO, Anthony; FINKE, Paul; ZANG, Yi; LIU, Weiguo; WO2012/24183; (2012); A1;,
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 3722-69-8 as follows. Quality Control of 8-Chlorochroman

Step 5, Method 2: Methyl (IS, 2S)-2-(8-chloro-3,4-dihydro-2H-l-benzopyran-6- carbonyl)cyclopropane-l-carboxylate [00160] Methyl (lS,2S)-2-(carbonochloridoyl)cyclopropane-l-carboxylate (0.19 g, 1.19 mmol) in DCE (2 mL) was added portionwise to a cooled (0 C), stirred solution of aluminium trichloride (0.32 g, 2.37 mmol) in DCE (4 mL) under a nitrogen atmosphere. 8- Chloro-3,4-dihydro-2H-l-benzopyran (0.2 g, 1.19 mmol) was added dropwise over 5 minutes and the reaction mixture was stirred at 0 C for a further 1 hour. After this time, the mixture was allowed to warm to room temperature before being stirred overnight. The reaction mixture was then cooled to 0 C before being added portionwise to a mixture of concentrated HC1 (4 niL) and ice (20 g). The resulting mixture was then extracted with DCM (3 x 50 mL), the combined organic extracts were washed with brine (30 mL), before being dried (MgS04), filtered and concentrated. The resulting residue was purified using a Biotage Isolera, (Snap 50 g cartridge, eluting in 0-45 % EtOAc in Heptanes) to give the title compound (0.15 g, 43% yield) as a pale yellow oil. deltaEta (250 MHz, CDCh) 7.88 (d, J= 2.1 Hz, 1H), 7.69 – 7.62 (m, 1H), 4.43 – 4.31 (m, 2H), 3.73 (s, 3H), 3.08 (ddd, J= 8.5, 5.9, 3.8 Hz, 1H), 2.86 (t, J= 6.4 Hz, 2H), 2.36 (ddd, J= 8.5, 6.1, 3.8 Hz, 1H), 2.16 – 1.96 (m, 2H), 1.58 (tdd, J= 7.6, 5.9, 3.4 Hz, 2H). Tr = 2.00 min m/z (ES+) (M+H+) 295.

According to the analysis of related databases, 3722-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; TOLEDO-SHERMAN, Leticia, M.; PRIME, Michael; MITCHELL, William; WENT, Naomi; WO2015/47978; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 892845-59-9, name is 1-Bromo-2-chloro-4-(trifluoromethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H3BrClF3O

1-bromo-2-chloro-4-(trifluoromethoxy)benzene (0.25 g, 0.91 mmol) was added to an flame dried 50 mL round-bottomed flask charged with a stir bar containing tetrahydrofuran (4.0 mL). The solution was placed under Ar2, cooled to -78 C. and n-butyllithium in hexanes (1.1 M, 0.83 mL) was added dropwise. The reaction proceeded for 5 min at -78 C. and then was quickly poured over dry ice. The solvents were evaporated in vacuo and the subsequent oil was partitioned between H2O and hexanes. The aqueous was washed with hexanes (3*10 mL) and then the aqueous was acidified with 1N HCl (10 mL). The product was extracted with EtOAc (3*20 mL), washed with brine (3*10 mL), dried over MgSO4, and concentrated in vacuo. 1H NMR (500 MHz, CDCl3-d) delta ppm 8.11 (d, J=8.7 Hz, 1H) 7.39 (d, J=1.7 Hz, 1H) 7.22 (dd, J=8.8, 1.7 Hz, 1H); HPLC Ret: 6.65 min.

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 892845-59-9.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY; Larsen, Scott D.; Neubig, Richard; Hutchings, Kim; Kahl, Dylan; Lisabeth, Erika Mathes; (56 pag.)US2019/308947; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1009102-44-6, name is 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, molecular formula is C9H11Cl2N, 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. COA of Formula: C9H11Cl2N

Step 2: To a suspension of 4-(4-chloiO-6-(2,2?2-trifluoroethoxy)-l,3,5-triazin-2- ylamino)faenzenesulfonamide from step 1 (1 g, 2.61 mmol) in THF (20 mL) was added l-(4-chlorophenyl)cyclopropanamine, HC1 (0.53 g, 2.61 mmol) and iPr2NEt (1.35 mL, 10.4 mmol). The mixture was heated at reflux condition for 16 hours. The solvent was removed under vacuum. The crude product 4-(4-(l -(4- chlorophenyl)cyclopropylamino)-6-(2}2,2-trifiuoroethoxy)-l,3J5-triazm-2- ylamino)benzenesulfonamide was used directly in the next step without further purification. LC-MS (Condition A), MS m/z 514.9 (M+ +H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1009102-44-6, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SUN, Li-Qiang; MULL, Eric; ZHAO, Qian; WANG, Tao; ZHANG, Zhongxing; SCOLA, Paul Michael; WO2012/24373; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 21402-26-6, name is 4-Bromo-3-chloroaniline, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

The product from example 32 step (ii) (O. 5g) and 4-bromo-3-chloroaniline (0. 38G) were dissolved in toluene (4ML). Ethanol (LML), 2M aqueous sodium carbonate (LML) and PD (PPh3) 4 (0. 115G) were added sequentially and the mixture heated at reflux for 4h. The reaction was cooled, evaporated, dissolved in EtOAc, washed with water and brine, dried (MGS04) and evaporated. The residue was purified by chromatography on silica eluting with 10% EtOAc/isohexane. Yield 0.23g. 1H NMR DMSO-d6 : 8 7.67 (ddd, 1H), 7.4 (d, 1H), 7.27-7. 34 (m, 6H), 7.01 (d, 1H), 6.7 (d, 1H), 6.55 (dd, 1H), 5.47 (s, 2H) 5.18 (s, 2H)

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; ASTRAZENECA AB; WO2004/89885; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics