Category: chlorides-buliding-blocks

Reference of 823-57-4, 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. 823-57-4, name is 2-Bromo-5-chloroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

HCl (500ml) for 2-bromo-5-chloroaniline (50 g, 242.16 mmol) and the mixture stirred at 0 while NaNO2 (17.5g, 253.62 mmol) to H2O (50ml) was added dropwise dissolved in a -10 after 1 hour It was stirred. The KI (44.2g, 266.26mmol) was stirred was dropwise added, dissolved in H2O (50ml) one hour at 0 . After completion of the reaction with ethyl acetate and filter the solidExtracts were dried over MgSO4 and the organic layer was filtered under reduced pressure. The filtered organic layer was evaporated under reduced pressure to a rear purified by column chromatography to the desired compound 1-bromo-4-chloro-2-iodobenzene (62 g,Yield: 66%) was obtained.

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

Reference:
Patent; Doosan Corporation; Kim, Tae Hyung; Bae, Hyung Chan; Lee, Chang Jun; Sin, Jin Yong; Jo, Hyun Chong; Baek, Young Mi; Rah, Jong Gyu; Park, Ho Chul; (46 pag.)KR2015/8658; (2015); A;,
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Some common heterocyclic compound, 2613-34-5, name is 3-Chloro-2,4-difluoroaniline, molecular formula is C6H4ClF2N, 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: C6H4ClF2N

Methyl 1 -methyl-4-[ [( 1R)-2,2,2-trifluoro- 1-methyl-ethyl] sulfamoyl]pyrrole-2-carboxylate (6.61 g, 21.03 mmol) and 3-chloro-2,4-difluoroaniline (4.13 g, 25.2 mmol) were dissolved in tetrahydrofuran (150 mL) and this was stirred and cooled in an ice-water bath. Over a period of 5minutes lithium bis(trimethylsilyl)amide in toluene (63.1 mL, 1 M, 63.1 mmol) was added dropwise. The resulting mixture was stirred for 1 h while cooling was continued. Another 2 eq of lithium bis(trimethylsilyl)amide in toluene (42.1 mL, 1 M, 42.1 mmol) were added and the resulting mixture was stirred for 1 hour at room temperature. The resulting mixture was quenched using ammonium chloride (sat. / 200 mL). The resulting mixture was extracted usingEtOAc (3 x 250 mL). The combined extracts were washed with brine (250 mL), dried on Na2SO4, filtered and concentrated in vacuo yielding a brown powder. This powder was crystallized twice out of methanol/water. The precipitation was collected on a glass filter. The obtained powder was purified by silica gel column chromatography using gradient elution from heptane to EtOAc (100:0 to 0:100). The obtained residue was crystallized again out ofmethanol/water. The white crystals were collected on a glass filter and dried in a vacuum oven at 55C for 24 hours yielding compound 120 (3.03 g) as a white powder. Differential scanning calorimetry: From 30 to 300 C at 10C/mm: peak at 217.6C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2613-34-5, its application will become more common.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 53145-38-3, name is 2-Chloro-6-fluoroanisole, 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 53145-38-3, Formula: C7H6ClFO

The system 100 shown in FIG. 1 was configured with a first reactor 102 having an internal volume of about 25 ml, a transfer tube 106 having an internal volume of about 3 ml and a second reactor 104 having an internal volume of about 30 ml.Agitation was started in the first reactor 102 and the second reactor 104. The system 100 was cooled to about -60 C. by placing the first reactor 102 and the second reactor 104 in the bath 108 containing dry ice in hexane and maintained at a temperature of about -70 C. A solvent level of the bath 108 was checked to assure that the transfer tube 106 was covered with the solvent.A solution of 2-chloro-6-fluoroanisole (2,6-CFA) (31.4 g, 190 mmol) in anhydrous 1,2-dimethoxyethane (DME) (241 ml) was prepared in a 500 ml bottle. Molecular sieves were added to remove water, and water content was measured by Karl Fischer titration to assure the 2,6-CFA solution contained less than about 100 ppm water (about 35 ppm measured). The 2,6-CFA solution in the 500 ml bottle was placed on a balance and fitted with a cap holding the inlet tube to metering pump 110. (i.e, first pump 110). A mixture of n-butyllithium in hexanes (2.5 M, 102 ml) was loaded into another (syringe) pump (i.e., second pump 112) and trimethyl borate (25.7 g, 28 ml) was loaded into a syringe and was placed on a separate syringe pump (i.e., third pump 114).The first, second, and third feed lines 118, 120, 122 were respectively pumped full of the 2,6-CFA, the n-butyllithium and the methyl borate to just short of the tube exit prior to the start of the experiment. When the solvent bath temperature was about -74 C., the first pump 110 containing the 2,6-CFA and the second pump 112 containing the n-butyllithium were started with flow rates of 0.73 ml/min and 0.27 ml/min, respectively. The first feed line 118 was formed from polytetrafluoroethylene (PTFE) tubing and was directed through the reactor head port 116A into the first reactor 102 below the liquid surface. The n-butyllithium addition was added to the first reactor 102 through the second feed line 120 that terminated just above the liquid surface in the first reactor 102.The solvent bath was monitored and dry ice was added to the solvent bath to maintain the temperature of the system 100 at less than about -60 C. The third feed line 122 for the trimethyl borate was directed into the second reactor 104 to drip above the liquid surface. After about 26 minutes, when the first reactor 102 was full and the reaction mixture was flowing through the transfer tube into the second reactor 104, the third pump 114 was started at a flow rate of the trimethyl borate of about 0.08 ml/min.After about 37 minutes, as the second reactor 104 filled, flow was started from an exit tube 126 to maintain reaction mixture volume in the second reactor 104 near about 30 ml. Intermediate solution from the second reactor 104 was accumulated in the flask 124 at room temperature. The intermediate solution was weighed and transferred to sample jars every 20 to 30 minutes. The experiment was run for 4 hours. A total of about 153 g of the intermediate solution containing PBA-diMe was collected. A gas chromatography (GC) method with internal standard was used to quantify the amount of PBA-diMe in the intermediate solution. A conversion to PBA-diMe of about 92% was calculated with about 8% of the original unconverted 2,6-CFA also quantified.

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-Chloro-6-fluoroanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DOW AGROSCIENCES LLC; Emonds, Mark V. M.; Menning, Catherine A.; Blaylock, D. Wayne; US2013/66115; (2013); A1;,
Chloride – Wikipedia,
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Related Products of 60811-21-4, These common heterocyclic compound, 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, 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.

[00367] Synthesis of 5-bromo-3-chloro-2-fluorobenzaldehyde (26): 4-Bromo-2-chloro- 1-fluorobenzene (25, 16 g, 76.5 mmol) was dissolved in 50 mL of THF. The reaction mixture was cooled down to -78 C. A solution of LDA in THF (2 M, 38.2 mL, 76.4 mmol) was added dropwise over 20 min. The reaction mixture was stirred at -78 C for 10 min. DMF (8.4 mL) was added dropwise. The reaction mixture was allowed to warm -20 C, quenched with 30 mL of saturated ammonium chloride aqueous solution and extracted with methyl fei -butyl ether (50 mL X 3). The combined organic layers were washed with brine, dried over anhydrous Na2S04, and concentrated under reduced pressure to give crude product, which was purified by silica gel chromatography (5-10% EtOAc/petroleum ether) to afford 8.4 g of 5-bromo-3-chloro-2-fluorobenzaldehyde (26) as white solid (yield: 46%). 1H MR (400 MHz, OMSO-d6) delta 10.10 (s, 1H), 8.26 (s, 1H), 7.93 (s, 1H).

Statistics shows that 4-Bromo-2-chloro-1-fluorobenzene is playing an increasingly important role. we look forward to future research findings about 60811-21-4.

Reference:
Patent; KARYOPHARM THERAPEUTICS INC.; BALOGLU, Erkan; SHACHAM, Sharon; SENAPEDIS, William; (155 pag.)WO2017/31204; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2106-02-7, name is 2-Chloro-4-fluoroaniline, 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. Computed Properties of C6H5ClFN

Production of ethyl (3S)-3-{[(2-chloro-4-fluorophenyl)amino]sulfanyl}-3,6-dihydro-2H-pyran-4-carboxylate To a solution (400 mL) of ethyl (3S)-3-sulfanyl-3,6-dihydro-2H-pyran-4-carboxylate (14.5 g) in dichloromethane was added dropwise tert-butyl hypochlorite (10 mL) at -78C. After stirring for 30 min, 2-chloro-4-fluoroaniline (23 mL) was added dropwise at -78C. The reaction mixture was stirred for 1 hr, and the reaction was discontinued with 5% aqueous sodium sulfite solution (300 mL). After extraction with dichloromethane (300 mL), the extract was washed with water, and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography (hexane/ethyl acetate=15:1?5:1) to give the title compound as a crude product (20.0 g, 96.3 %ee). This product was crystallized from diisopropyl ether/hexane (120 mL, 1:5) to give the title compound (12.3 g, 62%) as white crystals. 1H-NMR (CDCl3) delta: 1.33 (3H, t, J = 7.2 Hz), 3.72-3.79 (2H, m), 4.20-4.46 (5H, m), 5.53 (1H, br s), 6.90-7.03 (3H, m), 7.54-7.59 (1H, m). enantiomeric excess: >99 %ee [column: CHIRALPAK AD (manufactured by DAICEL CHEMICAL INDUSTRIES, LTD.), mobile phase: hexane/2-propanol = 97.5/2.5].

The synthetic route of 2106-02-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KITAMOTO, Naomi; (26 pag.)EP2528598; (2016); B1;,
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.

A. Tert-butyl N-(4-bromo-2-chlorophenyl)carbamate A solution of 4-bromo-2-chloroaniline (5.00 g, 0.0242 mol) in tetrahydrofuran (50 mL) was reacted with a 1.0 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (53.2 mL, 0.0532 mol). The mixture was stirred 15 minutes at ambient temperature. Di-tert-butyl dicarbonate (6.34 g, 0.0290 mol) was added and the solution was stirred for 2 hours. The solvent was removed in vacuo, and the crude material was purified by flash column chromatography on silica using heptane /ethyl acetate (4:1). The solvent was removed in vacuo to give tert-butyl N-(4-bromo-2-chlorophenyl)carbamate as a white solid (4.214 g, 0.0137 mol). 1H NMR (DMSO-d6, 400 MHz) delta 8.75 (s, 1H), 7.71 (d, 1H), 7.54 (d, 1H), 7.50 (dd, 1H), 1.46 (s, 9H); TLC (heptane/ethylacetate 4:1) Rf 0.54.

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; Abbott Laboratories; US2002/156081; (2002); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 6775-78-6, A common heterocyclic compound, 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, molecular formula is C6H4ClN3, 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 mixture of 6-chloroimidazo[1,2-b]pyridazine (3) 19 (768 mg, 5.0 mmol), 4-aminophenol (818 mg, 7.5 mmol), and K2CO3 (2073 mg, 15.0 mmol) in NMP (5 mL) was stirred at 120 C for 18 h. The mixture was diluted with 1 N aqueous NaOH and extracted with EtOAc. The organic layer was washed with 1 N aqueous NaOH and brine and concentrated in vacuo. The residue was purified by basic silica gel column chromatography (hexane/EtOAc 70:30 to 0:100) and triturated with diisopropyl ether to give 4a (759 mg, 67%) as a gray solid. 1H NMR (DMSO-d6) delta 5.07 (2H, s), 6.60 (2H, d, J = 8.9 Hz), 6.92 (2H, d, J = 8.9 Hz), 7.00 (1H, d, J = 9.8 Hz), 7.61 (1H, s), 8.01 (1H, s), 8.09 (1H, d, J = 9.8 Hz).

The synthetic route of 6775-78-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Miyamoto, Naoki; Oguro, Yuya; Takagi, Terufumi; Iwata, Hidehisa; Miki, Hiroshi; Hori, Akira; Imamura, Shinichi; Bioorganic and Medicinal Chemistry; vol. 20; 24; (2012); p. 7051 – 7058;,
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823-57-4, name is 2-Bromo-5-chloroaniline, 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. Formula: C6H5BrClN

Step 2: Preparation of Compound a26 (0680) (0681) To a solution of Compound a25 (1 g, 4.84 mmol) in pyridine (8 mL) was added sodium hydride (0.21 g, 5.33 mmol) and acetyl chloride (0.42 ml, 5.81 mmol), and the solution was stirred at 80° C. for 1 hour. To the reaction solution was added water, and the solution was extracted with ethyl acetate twice. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. To a solution of the obtained residue in THF/methanol (1:1, 9 ml) was added 2 mol/L sodium hydroxide aqueous solution (2.6 ml, 5.16 mmol), and the solution was stirred at room temperature for 30 minutes. To the reaction solution was added water, and the solution was extracted with ethyl acetate twice. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. To the obtained residue was added ethyl acetate (5 ml), and the mixture was dissolved in a water bath of 80° C. After cooled to room temperature, hexane (5 ml) was added to the solution, and the precipitated solid was filtered, washed with isopropyl ether (5 ml), and dried under reduced pressure to Compound a26 (674.4 mg, yield: 53percent) as a pale brown solid. (0682) 1H-NMR (CDCl3) delta: 8.46 (s, 1H), 7.59 (s, 1H), 7.45 (d, 1H, J=8.5 Hz), 6.97 (d, 1H, J=8.5 Hz), 2.25 (s, 3H).

The synthetic route of 823-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The University of Tokyo; TOHOKU UNIVERSITY; Shionogi & Co., Ltd.; NAGANO, Tetsuo; OKABE, Takayoshi; KOJIMA, Hirotatsu; KAWAGUCHI, Mitsuyasu; NUREKI, Osamu; ISHITANI, Ryuichiro; NISHIMASU, Hiroshi; AOKI, Junken; TANAKA, Nobuyuki; KANDA, Yasuhiko; KIOI, Yoshiyuki; TATENO, Yusuke; KIDA, Shiro; YAMANE, Junji; (163 pag.)US2017/158704; (2017); A1;,
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Electric Literature of 13526-66-4, 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 13526-66-4 as follows.

Example 1 (£)-2-(1-(3-((7-Fluoroquinolin-6-yl)methyl)imidazo[1 ,2-b]pyridazin-6-yl)ethylidene)- hydrazinecarboxamide6-Chloro-imidazo[1 ,2-b]pyridazin-3-yl)-(7-f luoro-quinolin-6-yl)-methanol (1.1 ) To a solution of 3-bromo-6-chloro-imidazo[1 ,2-b]pyridazine (13.27 g, 57.1 mmol) in 160 ml of THF was added EtMgBr (68.5 ml, 68.5 mmol) solution at room temperature. The reaction mixture was stirred for 30 min and a suspension of 7-Fluoro-quinoline-6-carbaldehyde (10 g, 57.1 mmol) in 40 ml of THF was added. The resulting mixture was stirred at roomtemperature for 3 hrs and quenched with 400 ml of water. After stirring for additional 1 hr, the precipitate was collected by filtration, washed with EtOAc and dried over vacuum oven overnight to afford 13 g (yield: 69%) of title compound. 1H-NMR (400MHz, DMSO-Cf6) delta ppm 8.91 (dd, 1 H), 8.49 (d, 1 H), 8.28 (d, 1 H), 8.24 (d, 1 H), 7.74 (d, 1 H), 7.54(q, 1 H), 7.51 (s, 1 H), 7.40 (d, 1 H), 6.54 (m, 2H).

According to the analysis of related databases, 13526-66-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; FU, Xingnian; HE, Feng; LI, Yue; LIU, Lei; MI, Yuan; XU, Yao-chang; XUN, Guoliang; YU, Zhengtian; ZHANG, Ji Yue (Jeff); DAI, Miao; WO2011/18454; (2011); A1;,
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Electric Literature of 1005-56-7, A common heterocyclic compound, 1005-56-7, name is O-Phenyl carbonochloridothioate, molecular formula is C7H5ClOS, 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.

The compound 24 (0.75 g, 1.75 mmol) was dissolved in anhydrous dichloromethane (20 mL) and phenyl chlorothionoformate (0.356 mL, 2.62 mmol) was added slowly at 0 C. After added pyridine (1.0 mL) the reaction mixture was stirred at for overnight and concentrated. The crude product was purified using silica gel column chromatography (10% EtOAc in Hexane) to give of desired 25 (0.94 g, 95%). 13C NMR (150MHz, CDCl3): d 166.19, 153.17, 133.79, 133.25, 130.04, 129.94, 129.75, 128.75, 128.53, 126.85, 122.08, 114.07, 101.34, 85.06, 80.07, 79.46, 78.88, 62.93, 26.29, 25.16.

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:
Article; Yu, Hai; Cao, Hongzhi; Tiwari, Vinod Kumar; Li, Yanhong; Chen, Xi; Bioorganic and Medicinal Chemistry Letters; vol. 21; 17; (2011); p. 5037 – 5040;,
Chloride – Wikipedia,
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