Category: chlorides-buliding-blocks

Synthetic Route of 203302-92-5, A common heterocyclic compound, 203302-92-5, name is 3-Bromo-2-chloro-6-fluorotoluene, molecular formula is C7H5BrClF, 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.

11. Reactions which are covered by Scheme 11; Example 11.1 : Preparation of (3-bromo-2-chloro-6-fluoro-phenyl)-acetic acid; Step 1; 3-Bromo-2-chloro-6-fluoro-toluene (8.0 g), N-bromosuccinimide (NBS) (6.42 g) and a catalytic amount of benzoyl peroxide in carbon tetrachloride (40 ml) were heated to reflux. A 500 watt tungsten halogen lamp was used to initiate the reaction. The reaction mixture was heated to reflux and irradiated for 30 minutes. The reaction mixture was allowed to cool and then filtered. The filtrate was concentrated to give a colourless oil which solidified on standing to give l-bromo-3-bromornethyl-2-chloro-4-fluorobenzene as an off-white solid (10.7 g). 1H NMR (CDCl3): 4.64 (d, 2H), 6.94 (t, IH), 7.58 (dd, IH) ppm.

The synthetic route of 203302-92-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA LIMITED; WO2008/9908; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 29671-92-9,Some common heterocyclic compound, 29671-92-9, name is Carbamimidic chloride hydrochloride, molecular formula is CH4Cl2N2, 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.

3.0 g of Arnold salt was added to 15 ml of methanol and 5 ml of water.Thereafter, 0.73 g of chloroformamidine hydrochloride and 0.53 g of sodium hydrogencarbonate were added thereto.The temperature was raised to 50 C to react. After 6 h of reaction, water was added to the system, and ethyl acetate was extracted.The opposite of water,The combined organic layers were washed with water, dried over anhydrous sodium sulfate and evaporatedThe yield was 83%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Carbamimidic chloride hydrochloride, its application will become more common.

Reference:
Patent; Anhui Haofan Biological Co., Ltd.; Lu Xuegen; Zhang Haiyan; Li Honglin; (6 pag.)CN109928933; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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. Application In Synthesis of 2,4-Difluorobenzene-1-sulfonyl chloride

General procedure: To 5-(5-(5-Aminopyridin-3-yl)thiophen-2-yl)-2-methyl- isoindolin-1-one (49) (225 mg, 0.79 mmol) in dry pyridine (23 mL) under N2 at RT,was added dropwise, 2,4-difluorobenzenesulphonyl chloride (336 mg, 1.58 mmol) in CH2Cl2(3 mL) over 5 min. The suspension was heated to 45 C under N2 for 4 h., at which pointanother portion of 2,4-difluorobenzenesulphonyl chloride (169 mg, 0.79 mmol) in CH2Cl2 (2mL) was added. The whole mixture was left to stir for at 45 C under N2 for 16 h., then thesolvent removed under reduced pressure. The resulting residue was suspended in acetone (10mL), 1 M HCl (20 mL) added, and the entire mixture stirred for 10 minutes. The solid wasthen collected by filtration, washed well with 1 M HCl and water, dried, and purified bychromatography as described below. In cases where the bis-sulphonamide was also formed, a second step was introduced wherethe crude product above was treated with a 1:1 mixture of 1,4-dioxane and 2 M NaOH. Thecrude sulphonamide resulting from subsequent acidification of the reaction mixture wasisolated by filtration, washed well with water, and dried. Purification was carried out by flashcolumn chromatography (2% MeOH/CH2Cl2 as eluant), giving the title compound as a paleyellow solid (211 mg, 545).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13918-92-8, its application will become more common.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 4; (2017); p. 1050 – 1054;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4863-91-6, name is 3-Chloro-5-fluoroaniline, 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 4863-91-6, COA of Formula: C6H5ClFN

Example 1: Synthesis of N-(3-chloro-5-fluorophenyl)-4 nitrobenzo[c] [1,2,5] oxadiazol-5-amine Compound 1 [093] 5-Chloro-4-nitrobenzo[c][l,2,5]oxadiazole (1 15 mg, 0.58 mmol) was combined with 3-chloro-5-fluoroaniline (83.7 mg, 0.58 mmol) in DMF (0.55 mL), and the mixture was heated at 110C for 1.25 hours. The mixture was cooled to ambient temperature, resulting in the formation of a solid mass. This solid was resuspended in ethyl acetate and transferred to a larger volume of ethyl acetate (100 mL). This was sonicated to completely dissolve the solids. The organic layer was washed 5 times with water (50 mL) and brine, separated, and dried over Na2S04, then filtered and concentrated in vacuo. The resultant yellow solid was resuspended in ethyl acetate (3 mL), and filtered. The solids were washed with fresh ethyl acetate, and air-dried. N-(3-chloro-5-fluorophenyl)-4-nitrobenzo[c][l,2,5]oxadiazol-5-amine was obtained as a free-flowing yellow solid, (122 mg, 69%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-5-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; BRUICK, Richard, K.; CALDWELL, Charles, G.; FRANTZ, Doug, E.; GARDNER, Kevin, H.; MACMILLAN, John, B.; SCHEUERMANN, Thomas, H.; TAMBAR, Uttam, K.; WO2014/78479; (2014); A2;,
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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, A new synthetic method of this compound is introduced below., COA of Formula: C13H11ClFNO

A stirred suspension of 3H-6-iodoquinazolin-4-one (compound A) in toluene (5 vols) was treated with tri-n-butylamine (1.2 eq.) at 20 to 250C, then heated to 900C. Phosphorous oxychloride (1.1eq) was added, the reaction mixture was then heated to reflux. The reaction mixture was cooled to 500C and toluene (5vols) added. Compound C (1.03 eq.) was added as a solid, the slurry was warmed back to 900C and stirred for 1 hour. The slurry was transferred to a second vessel; the first vessel was rinsed with toluene (2vol) and combined with the reaction mixture. The reaction mixture was cooled to 700C and 1.0 M aqueous sodium hydroxide solution (16 vols) added dropwise over 1 hour to the stirred slurry maintaining the contents temperature between 68-72C. The mixture was stirred at 65-700C for 1 hour and then cooled to 200C over 1 hour. The suspension was stirred at 200C for 2 hours, the product collected by filtration, and washed successively with water (3 x 5 vols) and ethanol (IMS, 2 x 5 vols), then dried in vacuo at 50-600C. Volumes are quoted with respect of the quantity of Compound A used. Percent yield range observed: 90 to 95% as white or yellow crystals.

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; SMITHKLINE BEECHAM (CORK) LIMITED; WO2006/66267; (2006); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 14862-52-3, A common heterocyclic compound, 14862-52-3, name is 3,5-Dibromochlorobenzene, molecular formula is C6H3Br2Cl, 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.

3 -Bromo-5 -chlorophenvDmethylformamide l,3-Dibromo-5-chlorobenzene (1.0 g, 3.7 mmol), N-methylformamide (0.26 mL, 4.4 mmol), CuI (35 mg, 0.02 mmol), N,N’-dimethyl ethylenediamine (0.04 mL, 0.37 mmol) and K2CO3 (1.02 g, 7.4 mmol) in 1,4-dioxane (4 mL) were heated to 110 0C in a sealed tube for 20 h. The blue slurry was diluted with EtOAc (10 mL) and filtered through a short silica plug that was washed with several portions of EtOAc. The solvent was removed by evaporation and the resulting yellow oil was purified by flash chromatography using 70 g silica and a gradient of 0%EtOAc to 50%EtO Ac/Heptane. The subtitle compound was obtained as a colourless solid (385 mg, 41%).1H-NMR (CDCl3): delta 8.52 (IH, s), 7.43 (IH, t), 7.24 (IH, t), 7.13 (IH, t), 3.30 (3H, s); GC-MS m/z: 247/249/251 [M+].

The synthetic route of 14862-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/7747; (2009); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 627-42-9, name is 2-Methoxyethyl chloride, 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. Application In Synthesis of 2-Methoxyethyl chloride

A pressure glass vessel charged with 1-(4-hydroxy-2,6-dimethylphenyl)ethanone (500 mg, 3.1 mmol, 1.0 equiv) and 1-chloro-2-methoxyethane (0.28 nL, 3.1 mmol, 1.0 equiv) in 50% aqueous NaOH solution (5.0 mL) was heated at 140 C for 16 h. The residue was diluted with H2O (20 mL) and extracted with EtOAc (3 X 30 mL). The organic layer was separated, dried with MgSO4, and concentrated under reduced pressure to give 1-(4-(2-methoxyethoxy)-2,6-dimethylphenyl)ethanone (430.9 mg, 1.9 mmol) as yellow oil in 64% yield: 1H NMR (CDCl3, 500 MHz) delta 6.58 (s, 2 H), 4.09-4.10 (m, 2 H), 3.72-3.74 (m, 2 H), .44 (s, 3 H), 2.45 (s, 3 H), 2.23 (s, 6 H); ESI-MS: m/z 223.6 (M + H)+.

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

Reference:
Patent; TAIVEX THERAPEUTICS CORPORATION; HUANG, Yu-Ling; CHUANG, Shih-Hsien; LEE, Ying-Shuan Eda; HUANG, Jiann-Jyh; LAU, Johnson; WO2013/82324; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 870-24-6, The chemical industry reduces the impact on the environment during synthesis 870-24-6, name is 2-Chloroethanamine hydrochloride, I believe this compound will play a more active role in future production and life.

Example 16 5-Cyclopropyl-6-(1,1-dioxo-1lambda6-[1,2,5]thiadiazolidin-2-yl)-2-(4-phenoxy-phenyl)-benzofuran-3-carboxylic acid methylamide (I-102) A solution 2-chloroethyl amine hydrochloride (0.348 g, 3.0 mmol) and sulfuryl chloride (18 mL, 18 mmol) in MeCN (25 mL) was heated overnight at 80 C. then cooled and evaporated to afford N-(2-chloroethyl)-sulfamoyl chloride (60).

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, 2-Chloroethanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Roche Palo Alto LLC; US2009/208449; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 461432-23-5, A common heterocyclic compound, 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, molecular formula is C15H14BrClO, 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.

Boron tribromide (1.7 mL, 16.89 mmol) was added at 0 &Of dichloromethane (10 mL)Was slowly added dropwise to a solution of 2- (4-methoxyphenyl) -4-bromo-1-chlorobenzene 1f (5.0 g, 15.35 mmol, purchased from Shanghai Lu Lu Lan Co., Ltd.) in dichloromethane (50 mL) ,Rise to room temperature for 30 minutes.The pH was adjusted to 7 with saturated aqueous sodium bicarbonate solution,And then extracted with dichloromethane (50 mL x 2). The combined organic phases were washed with saturated brine (30 mL x 2), dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure.The title compound was obtained as a pale yellow solid (5.16 g, 100%). The crude product is used directly in the next step.

The synthetic route of 461432-23-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Gu Zheng; Wu Wuyong; Qu Tong; Tan Haoxiong; Kang Panpan; Deng Bingchu; (48 pag.)CN106892948; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 139512-70-2, 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. 139512-70-2 name is 4-Chloro-5-fluorobenzene-1,2-diamine, 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.

General procedure: A mixture of compounds 1a-l (0.013 mol) and 4-chloro-5-fluoro-ophenylenediamine(2) (0.01 mol) in methanol (10 mL) was irradiatedwith ultrasonic irradiation at 50 C for 7 min (8 min for 3a) Afterreaction completion (monitored by TLC, ethyl acetate/hexane = 3:1), themixture was poured onto water and the precipitated product was filtrated off, washed with water and recrystallised from ethanol/water, 3:1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloro-5-fluorobenzene-1,2-diamine, and friends who are interested can also refer to it.

Reference:
Article; Mente?e, Emre; Kahveci, Bahittin; Mente?e, Meltem; Journal of Chemical Research; vol. 42; 6; (2018); p. 329 – 331;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics