Tag: M.W=200-300

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. 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, A new synthetic method of this compound is introduced below., Quality Control of 4-Bromo-2-chloro-1-fluorobenzene

A dry, argon-flushed Schienk-flask equipped with a magnetic stirrer and a septum was charged with 20 mL freshly titrated iPrMgClLiCI (1.24 M in THE, 1.0 equiv.) to which 3.8 mL of diisopropylamine (1.1 equiv.) was added dropwise at 25 00. The reaction mixture was stirred at this temperature until gasevolution was completed (ca. 48 h). The formed precipitate was dissolved with additional dry THE. The fresh solution of iPr2NMgCILiCI in THE was titrated at 25 00 with benzoic acid and 4- (phenylazo)diphenylamine as an indicator. A concentration of 0.59 M was obtained.To a solution of 4-bromo-2-chloro-1 -fluoro-benzene (0.209 g, 1 .00 mmol) in THE (1 mL) was added iPr2NMgCILiCI (0.59 M, 3.39 ml, 2.00 mmol) at 25 00 and the resulting mixture was stirred for 15 mm at25 c Hexachloro-2-propanone (0.397 g, 1 .50 mmol) was added at 0 00 and the mixture was stirred for15 mm. The resulting mixture was then quenched with sat. aq. NH4CI, extracted with ethyl acetate and dried over anhydrous Na2SO4. After filtration, the solvent was removed in vacuo. Quantitative GO measurement showed that the ratio between 5-bromo-1 ,3-dichloro-2-fluoro-benzene and regioisomer is about 12:1. Purification by flash column chromatography (Si02, i-hexane) furnished 5-bromo-1 ,3-dichloro-2-fluoro-benzene (0.190 g) as a colorless oil.

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; SYNGENTA PARTICIPATIONS AG; SMITS, Helmars; KNOCHEL, Paul; KLATT, Thomas; BECKER, Matthias; (18 pag.)WO2016/58895; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 38762-41-3,Some common heterocyclic compound, 38762-41-3, name is 4-Bromo-2-chloroaniline, molecular formula is C6H5BrClN, 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.

Compound alpha (1 g, 4.8 mmol) was dissolved in 10 mL of anhydrous methylene chloride. To this mixture was added triethylamine (0.68 mL, 4.8 mmol) and the reaction was stirred at room temperature for 5 min. Acetyl chloride (0.5 mL, 7.2 mmol) was then added at 0 0C and the mixture stirred at room temperature for 2 hours. Water and dichloromethane were added and the layers separated. The organic layer was then dried over sodium sulfate and concentrated to give 1.11 g, 92% yield of compound b. To a solution of b (500 mg, 2.01 mmol), cyclopropyl boronic acid (225 mg, 2.62 mmol), potassium phosphate (1.49 g, 7.04 mmol) and tricyclohexylphosphine (56 mg, 0.2 mmol) in toluene (10 mL) and water (0.4 mL) under nitrogen atmosphere was added palladium acetate (23 mg, 0.1 mmol). T he mixture was heated to 100 0C for 3h and then cooled to room temperature. Water was added and the mixture extracted with ethyl acetate, dried over sodium sulfate and concentrated to give 550mg of crude product c that was used in the next step without further purification. Compound c (500mg, 2.4 mmol) was dissolved in 4 mL of ethanol. Aqueous IN HCl (4 mL) was added and the mixture stirred at reflux for 8 hours. The solvent was removed in vacuo to afford 440mg of compound d which was used in the next step without further purification. Compound d (440mg, 2.6 mmol) was dissolved in 14 mL of dichloromethane. Sodium bicarbonate (7 mL, sat. solution) and thiophosgene (0.2 mL, 2.6 mmol) were added and the mixture stirred at room temperature for Ih. Then, the organic layer was separated, dried over sodium sulfate and concentrated to afford 877 mg, 99% yield of compound e which was used in the next step without further purification Compound e (447mg, 2.1 mmol) was dissolved in 3 mL of dimethylformamide, aminoguanidine hydrochloride salt (355 mg, 3.2 mmol) and diisopropyl ethylamine (0.56 mL, 3.2 mmol) were added and the mixture stirred at 50 0C for 18 hours. The mixture was then concentrated and to the resulting residue was added 2M aqueous sodium hydroxide solution (10 mL). The mixture was stirred at 50 0C for 18 hours and then cooled to room temperature. The resulting mixture was then neutralized with aqueous IN HCl and the precipitate (product) collected to give compound/ (240 mg, 44% yield) Compounds/(89mg, 0.33 mmol) and g (94mg, 0.33 mmol) were dissolved in DMF (1.5 mL) and potassium carbonate (51mg, 0.37 mmol) was added. The mixture was stirred at room temperature for 18 hours. Water was then added to the mixture and the precipitate formed collected and purified by prep. TLC (90% dichloromethane/ 10% methanol) to give 116 mg, 68% yield of compound h. Dichloroacetic acid (0.04 mL, 0.46 mmol) was added to a mixture of compound h (116mg, 0.23 mmol), benzyltriethyl ammonium bromide (183mg, 0.68 mmol) and sodium nitrite (304mg, 4.6 mmol) in dibromomethane (5 mL). The mixture was stirred at room temperature for 18 hours in the dark. The reaction mixture was then concentrated and the resulting residue was purified by prep. TLC (95% dichloromethane /5% methanol) to afford 99.10 mg of the sulfonic acid and 17.90 mg of title compound i.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2-chloroaniline, its application will become more common.

Reference:
Patent; VALEANT RESEARCH & DEVELOPMENT; WO2006/26356; (2006); A2;,
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. Quality Control of 4-Bromo-2-chloro-1-methoxybenzene

To a 3-necked round bottom flask was added 4-bromo-2-chloro-1-methoxy-benzene(45.00 g, 203.18 mmol) and THF (450 mL), n-Butyllithium (2.5 M in hexanes, 90.21 mL, 1.11 eq) was added at -78 C. The mixture was stirred for 2 h at -78 C. A solution of 1,4- dioxaspiro[4.5]decan-8-one (34.91 g, 223.50 mmol) in THF (90 mL) was added dropwise to the reaction mixture. The resulting mixture was stirred for 3 h at -78 C. The reaction was quenched with aqueous NH4C1 (lOOmL) and extracted with EtOAc (500 mL). The organic layer was dried (Na2504), filtered and concentrated. The residue was washed with hexanes (350 mL), filtered and dried under high vacuum. The solid was triturated with hexanes (15 mL), filtered and dried under high vacuum to give 8-(3-chloro-4-methoxy-phenyl)-1,4- dioxaspiro[4.5]decan-8-ol (37 g, 61%) as a white solid. ?H NMR (400 IVIHz, CDC13): 7.31 (d, 1H), 7.29 (dd, 1H), 7.10 (d, 1H), 3.90-3.92 (m, 4H), 3.89 (s, 3H), 1.99-2.02 (m, 4H), 1.70- 1.73 (m, 4H); LCMS: 281.2 [M-OH].

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

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; NAGASAWA, Johnny Y.; (169 pag.)WO2018/170166; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 50594-82-6, name is 3,4,5-Trichlorobenzotrifluoride, molecular formula is C7H2Cl3F3, 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. HPLC of Formula: C7H2Cl3F3

Comparative Example 3: Preparation of 2,6-dichloro-4-(trifluoromethyl)phenyl- hydrazine of the formula 1-1 from 3,4,5-trichloro- benzotrifluoride in toluene; 10 g (40 mmole) of 3,4,5-trichlorobenzotrifluoride (99.7% purity) were dissolved in 30 g (326 mmole) of toluene. To this solution were added 8 g (160 mmole) of hydrazine hydrate (100%). The resulting mixture was stirred at reflux (approx. 1100C) for 24 hours. Thereafter, an organic phase of 39.4 g was separated. The solution obtained by this separation contained the product 2,6-dichloro-4-(trifluoromethyl)phenylhydrazine in an amount of 0.9 wt-% and the starting material 3,4,5-trichlorobenzotrifluoride in an amount of 26.3 wt-%, meaning that a product yield not higher than 3.6 % was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 50594-82-6, its application will become more common.

Reference:
Patent; BASF SE; WO2008/113661; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 63624-28-2,Some common heterocyclic compound, 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl chloride, molecular formula is C8H9ClO4S, 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 1 3-Amino-5-chloro-1,3-dihydro-1-(2,4-dimethoxybenzenesulfonyl)-3-phenylindol-2-one A solution of 0.3 g of 3-amino-5-chloro-1,3-dihydro-3-phenylindol-2-one in 7 ml of DMF is cooled to 0 C. under an argon atmosphere and 0.037 g of sodium hydride as an 80% dispersion in oil is added. After stirring for 20 minutes, 0.275 g of 2,4-dimethoxybenzenesulfonyl chloride is added and the reaction mixture is stirred overnight, the temperature being allowed to rise to RT. It is poured into water, extracted with AcOEt, washed with water and with a saturated solution of NaCl, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on silica using a DCM/AcOEt mixture (95/5; v/v) as the eluent to give the expected product after crystallization from a DCM/iso ether/hexane mixture. m=0.31 g. M.p.=108-110 C.

The synthetic route of 63624-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sanofi; US5594023; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 61881-19-4, A common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, molecular formula is C8H5ClF3N, 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: Add sodium acetate, trifluoroethylimidyl chloride (II), hydrazone (III), and 1 mL of organic solvent to the 35 mL Schlenk tube according to the raw material ratio in Table 1.Mix and stir well. After the reaction is completed according to the reaction conditions in Table 2, 2-4 hours,Add elemental iodine, continue the reaction for 1-2 hours, filter, and stir the sample in silica gel.After purification by column chromatography, the corresponding 5-trifluoromethyl-substituted 1,2,4-triazole compound (I) is obtained. The reaction process is shown by the following formula:

The synthetic route of 61881-19-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Sci-Tech University; Chen Zhengkai; Hu Sipei; Yang Zuguang; (10 pag.)CN110467579; (2019); A;,
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. 27139-97-5, name is 2-Bromo-4-chloro-1-methylbenzene, A new synthetic method of this compound is introduced below., Safety of 2-Bromo-4-chloro-1-methylbenzene

Step 1 5-chloro-2-methylbenzaldehyde To a solution of 2-bromo-4-chlorotoluene (20.0 g; 97.3 mmol) in 300 mL of THF at -78¡ã C. was added dropwise a 2.5 M solution of n-BuLi (102.2 mmol). After 30 min of stirring at that temperature, 1-formylpiperidine (11.4 mL) in 10 mL of THF was added and the solution left for 1 h. It was brought to 0¡ã C., quenched with NH4OAc (25percent) and diluted with EtOAc. The organic phase was dried over Na2SO4, filtered and the solvent removed to yield 13.3 g of the title compound. 1H NMR (CDCl3) delta2.6 (3H, s), 7.15 (1H, d), 7.4 (1H, d), 7.75 (1H, s) and 10.2 (1H, s).

The synthetic route of 27139-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Frosst Canada & Co.; US6242493; (2001); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 928783-85-1, name is 1-Bromo-3-chloro-5-(trifluoromethyl)benzene, 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 928783-85-1, Formula: C7H3BrClF3

A solution of 1-bromo-3-chloro-5-(trifluoromethyl)benzene (5.0 g), 3-hydroxypyrrolidine (1.85 g), palladium(II) acetate (217 mg), (+/-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.2 g) and cesium carbonate (18.8 g) in toluene (96 mL) was stirred under an argon gas atmosphere at 85 C. for 16 hr. After cooling to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate 80:20-10:90) to give the title compound (4.11 g, yield 80%) as a brown oil.1H-NMR (300 MHz, CDCl3) delta: 1.65 (d, J=3.8 Hz, 1H), 2.00-2.29 (m, 2 H), 3.19-3.32 (m, 1H), 3.38 (td, J=8.7, 3.4 Hz, 1H), 3.45-3.60 (m, 2H), 4.58-4.72 (m, 1H), 6.61 (s, 1H), 6.63-6.68 (m, 1H), 6.88 (s, 1H).

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, 1-Bromo-3-chloro-5-(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kasai, Shizuo; Kamaura, Masahiro; Cho, Nobuo; US2011/251187; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 19752-55-7, 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. 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Add 2.2 g of 1-bromo-3,5-dichlorobenzene (0.01 mol) to the reaction flask. 2.3 g of potassium 2,2,2-trifluoroacetate (0.015 mmol), 2.3 g of iodinated ketone (0.012),1.04 g of pyridine (0.013 mol), 10 ml of N-methylpyrrolidone, refluxed at 200 C for 1 hour, and the solvent was evaporated to give a crude compound 1.94 g. Then, after mixing 10 ml of H2SO4 and 5 ml of HNO3, the crude compound 1 was slowly added at 0 C. After the reaction for 2 hours, the reaction was stopped, and the mixture was poured into ice water and suction filtered to give the desired fipronil intermediate 2.19 g in a yield of 86.2%.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3,5-dichlorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Jiangsu Changqing Agrochemical Co., Ltd.; Yu Guoquan; Sun Xialin; Ma Changqing; Ding Huaping; (5 pag.)CN109369403; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 56961-77-4, 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. 56961-77-4 name is 1-Bromo-2,3-dichlorobenzene, 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.

To 1-bromo-2,3-dichlorobenzene [r-1] (22.6 g, 100 mmol), sodium t-butoxide (29.6 g, 308 mmol), 2,2?-bis (diphenylphosphino)-1 , 1 ?-binaphthyl [I3INAP] (2.51 g, 4.0 mmol), bis(dibenzylideneacetone) palladium (0) [Pd2 (dba) 31(1.83 g, 2.0 mmol), and toluene (400 ml), aniline [r-2] (18.5 ml, 203 mmol) was added under a nitrogen atmosphere at room temperature, and the resulting mixture was heated and stirred at 1000 C. for 26 hours. The reaction solution was cooled to room temperature, and was filtered using silica gel column chromatography, and a solvent was distilled oil under reduced pressure to obtain a crude product. Thereafier, the resulting crude product was washed with toluene to obtain 2-chloro-N,N?-diphenyl- 1 ,3-benzenediamine [r-3] (18.4 g, yield 63%) as a white solid. The structure of the compound thus obtained was identified with an NMR spectrum. 1H-NMR (400 MHz, CDC13): &6.08 (s, 2H), 6.80 (s, 2H), 6.99 (t, 1H), 7.04 (U, J=1.1, 7.3 Hz, 2H, (CH)2CH (CR2)2), 7.18 (dd, 4H), 7.32 (dd, 4H). 13C-NMR (101 MHz, CDC13): 107.1 (2C), 109.4,120.4 (4C), 122.5 (2C), 127.0, 129.3 (4C), 141.1 (2C), 141.6 (2C).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2,3-dichlorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Kwansei Gakuin Educational Foundation; JNC Corporation; Hatakeyama, Takuji; NAKATSUKA, Soichiro; GOTOH, Hajime; SASADA, Yasuyuki; YANAI, Motoki; IKUTA, Toshiaki; (337 pag.)US2018/69182; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics