Tag: M.W=200-300

Reference of 329944-72-1, 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. 329944-72-1 name is 3-Bromo-5-chlorotoluene, 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.

1-(3,5-difluorophenyl)-1,2,4-triazol-3-amine (1.12 g, 5.710 mmol), 1-bromo-3-chloro-5-methyl-benzene (2.72 g, 13.24 mmol), sodium tert-butoxide (approximately 909.8 mg, 9.467 mmol) and chloro(2-di-t-butylphosphino-2′,4′,6′-tri-i- propyl-1,1′ -biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) (t-BuXPhos Palladacycle) (approximately 227.4 mg, 0.3078 mmol) were slurried into dry t- butanol (15.86 mL) and dry 1,4-dioxane (5.288 mL) and purged with nitrogen for -10 minutes. The reaction was sealed and stirred at 90 C for ~1 hour. The reaction mixture was cooled to room temperature and poured into water (150 mL). The precipitate was filtered. The filter cake was washed with additional water (-75 mL) and methanol (-25 mL). Dried the filter cake in the high vacuum oven at 50C overnight to yield N-(3-chloro-5-methyl-phenyl)-1-(3,5-difluorophenyl)-1,2,4-triazol- 3-amine (1.587 g, 4.629 mmol, 81%). NMR (300 MHz, DMSO-^e) delta 9.78 (s, 1H), 9.20 (s, 1H), 7.68 – 7.58 (m, 2H), 7.55 (d, J = 1.9 Hz, 1H), 7.34 (s, 1H), 7.28 (tt, J = 9.4, 2.3 Hz, 1H), 6.76 (s, 1H), 2.29 (s, 3H) ppm. ESI-MS m/z calc. 320.06403, found 321.07 (M+l)+; Retention time: 1.02 minutes.

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; BETHIEL, Randy Scott; CAO, Jingrong; COLLIER, Philip, N.; DAVIES, Robert J.; DOYLE, Elisabeth; FRANTZ, James Daniel; GOLDMAN, Brian Anthony; GREY, Ronald Lee; GRILLOT, Anne-laure; GU, Wenxin; KOLPAK, Adrianne Lynne; KRAUSS, Paul Eduardo; LIAO, Yusheng; MAGAVI, Sanjay Shivayogi; MESSERSMITH, David; PEROLA, Emanuele; RYU, Elizabeth, Jin-Sun; SYKEN, Joshua; WANG, Jian; (491 pag.)WO2018/106646; (2018); A1;,
Chloride – Wikipedia,
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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., Recommanded Product: 202197-26-0

Step A: Preparation of 4-[3-chloro-4-(3-fluoro-benzyloxy)phenylamino]-6-nitro-quinazoline 1.20 g (5.7 mmol) of 4-chloro-6-nitro-quinazoline (prepared by referring to WO 2007/082434) and 1.37 g (5.6 mmol) of 4-(3-fluoro-benzyloxy)-3-chloro-aniline (prepared by referring to WO 2007/082434) were dissolved in 80 mL of isopropanol and refluxed for 3 hours. A large amount of yellow solid was precipitated from the system, and was filtered. The filter cake was washed with a saturated sodium bicarbonate aqueous solution till pH=8 and dried under vacuum to give 1.62 g (3.75 mmol) of yellow solid, which was identified as 4-[3-chloro-4-(3-fluoro-benzyloxy)phenylamino]-6-nitro-quinazoline with a yield of 67%. 1H-NMR (400 MHz, CDCl3): delta 11.30(1H, br), 9.54-9.48 (1H, m), 8.45-8.41 (1H, m), 8.31-8.25 (1H, m), 7.98-7.89 (1H, m), 7.50-7.47 (1H, m), 7.35-7.26 (1H, m), 7.05-6.96 (1H, m), 6.90-6.80 (2H, m), 7.74-7.60 (2H, m), 4.84 (2H, s).

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; Guo, Jianhui; He, Haiying; US2011/111059; (2011); A1;,
Chloride – Wikipedia,
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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. 174913-10-1, name is 1-Bromo-3-chloro-2-methoxybenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 1-Bromo-3-chloro-2-methoxybenzene

EXAMPLE 217 7-Chloro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 317, structure 88 of Scheme XXIV, where R1 =chloro, R2-6 =H, R7-9 =methyl) 3-Chloro-2-methoxyphenylboronic acid (structure 90 of Scheme XXIV, where R1 =chloro, R2-4 =H) This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-6-chloroanisole (0.71 g, 3.2 mmol), n-BuLi (2.5M in hexanes; 1.28 mL, 3.2 mmol), and trimethylborate (1.09 mL, 9.6 mmol) to afford 0.55 g (91%) of 3-chloro-2-methoxyphenylboronic acid which was used without further purification.

The synthetic route of 174913-10-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688808; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 14862-52-3, These common heterocyclic compound, 14862-52-3, name is 3,5-Dibromochlorobenzene, 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.

Potassium phosphate mono-hydrate (K3PO4.H2O, 8 g, 40 mmol, 2 equiv) and 1-chloro-3,5-dibromobenzene (2.4 g, 8.93 mmol) were added into the reaction solution of EXAMPLE 2, then refluxed at 110 C. overnight under argon atmosphere. Then cooled to ambient temperature. Distilled water (30 mL) was added via a funnel, and the resulting mixture was filtered on a Buechner funnel. The filtrate was transferred to a separatory funnel and extracted with CH2Cl2 (3¡Á50 mL). The combined organic phases were dried over Na2SO4, filtered on filter paper and concentrated to dryness by rotary evaporation (30 C., 25 mmHg). The resulting yellow solid was purified by column chromatography to afford 3.33 g white solid (90%). Compound G: 1H NMR (400 MHz, CDCl3). 8.97 (s, 2H), 8.67 (d, 2H), 8.08 (d, 2H), 7.84 (s, 2H), 7.76(s,1H), 7.73-7.71(m, 2H), 7.66-7.63 (m, 6H), 7.54-7.50 (m, 2H).

Statistics shows that 3,5-Dibromochlorobenzene is playing an increasingly important role. we look forward to future research findings about 14862-52-3.

Reference:
Patent; General Electric Company; US2010/331547; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 328-84-7, These common heterocyclic compound, 328-84-7, name is 3,4-Dichlorobenzotrifluoride, 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 15 Preparation of Compound No. 77 To a solution of 5-nitroindazole in N,N-dimethylformamide (20 g), 60% sodium hydride (0.5 g) was added slowly, and the resultant mixture was stirred while cooling with ice for 30 minutes. To the mixture, 3,4-dichlorobenztrifluoride (2.2 g) was added, and the resultant mixture was stirred at 80 C. for 2 hours. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was concentrated and the residue was purified by silica gel column chromatography with hexane-ethyl acetate (4:1) to give 1-(2-chloro-4-trifluoromethylphenyl)-5-nitroindazole (2.1 g).

The synthetic route of 328-84-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; US5266556; (1993); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 24279-39-8, These common heterocyclic compound, 24279-39-8, name is 2,6-Dichloro-4-(trifluoromethyl)aniline, 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.

CuBr2 (4.02 g, 18.0 mmol) and tert-butyl nitrite (3.12 g, 30.3 mmol)were added together with MeCN (60 mL) to a three-necked flask underargon. In a separate flask, 2,6-dichloro-4-trifluoromethylaniline(3.5 g, 15.2 mmol) was dissolved in MeCN (20 mL) under argon. Theaniline solution was then added dropwise to the three-necked flaskcontaining the nitrite mixture. The reaction mixture was then heatedto 65 C and stirred overnight. The mixture was cooled to r.t. andpoured into a separatory funnel with H2O (50 mL) and Et2O (110 mL).The organic layer was separated and washed with aq 3 M HCl (2 ¡Á 30mL). The organic layer was dried (Na2SO4), concentrated by rotaryevaporation and high vacuum to completely remove the volatiles;yield: 3.79 g (85%); colorless oil.1H NMR (300 MHz, CDCl3): delta = 7.63 (s, 2 H).13C NMR (100 MHz, CDCl3): delta = 137.4, 131.1 (q, J = 34 Hz), 127.9, 125.2(q, J = 3.1 Hz), 122.4 (q, J = 271 Hz).

Statistics shows that 2,6-Dichloro-4-(trifluoromethyl)aniline is playing an increasingly important role. we look forward to future research findings about 24279-39-8.

Reference:
Article; Miller, Daniel K.; Bailey, Christopher A.; Sammelson, Robert E.; Synthesis; vol. 47; 18; (2015); p. 2791 – 2798;,
Chloride – Wikipedia,
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6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, 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: C6H3Cl3O2S

2,6-Dichloro-3-nitrobenzenesulfonic acid Lithium hydroxide hydrate (8.96 g, 0.214 mol) was added to a solution of 2,6-dichlorobenzenesulfonyl chloride (35 g, 0.146 mol) in MeOH (300 mL) and the reaction was allowed to stir at room temperature for 16 hr. The reaction mixture was filtered to remove suspended solids and then concentrated. The resulting solid was dried in vacuo overnight to remove any residual MeOH. The solid was then dissolved in H2SO4 (300 mL) and chilled in an ice bath. A solution of H2SO4 (35 mL) and HNO3 (70%, 10.7 mL) was slowly added to the above reaction over 90 min. The reaction was allowed to warm up to room temperature overnight and then slowly poured into ice water (1200 mL) and extracted with EtOAc. The combined organic layers were dried (MgSO4) and concentrated to yield 2,6-dichloro-3-nitrobenzenesulfonic acid (37.38 g, 96%) as the dihydrate. EI-MS (m/z) 270 (M-).

The synthetic route of 6579-54-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Palovich, Michael R; Widdowson, Katherine L; Nie, Hong; US2003/50298; (2003); A1;,
Chloride – Wikipedia,
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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. 3386-33-2, name is 1-Chlorooctadecane, A new synthetic method of this compound is introduced below., Quality Control of 1-Chlorooctadecane

REFERENCE EXAMPLE 30 Preparation of (1R,2R)-2-(Stearoylamino)cyclohexanol (1R,2R)-2-Aminocyclohexanol (1.15 g) and 3.02 g of stearyl chloride were reacted in the same manner as in Reference Example 20 to obtain 3.0 g of the objective compound (yield: 100%). Property: Oily. Mass Spectrometric Analysis: Molecular formula: C24 H47 NO2, Calculated: 381.3606, Found: 381.3611. NMR(delta, CDCl3): 0.88 (3H,t,J=7Hz), 1.11-1.41 (32H,m), 1.57-1.78 (4H,m), 1.89-2.11 (2H,m), 2.22 (2H,t,J=7Hz), 3.31 (1H,ddd,J=11Hz,11Hz, 5Hz), 3.58-3.70 (1H,m), 5.42-5.51 (1H,m).

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; Fujirebio Inc.; US5120738; (1992); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, 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: C6H3BrCl2

Magnesium turning (2.8 g) and iodine (50 mg) were added to a 250 mL three-necked round bottom flask and stirred under an argon atmosphere for 30 minutes. 1-bromo-3,5-dichlorobenzene (20.7 g) dissolved in tetrahydrofuran was slowly added dropwise, heated to reflux for 2 hours, and then cooled to room temperature. In another round bottom flask, trimethoxyboraine (33.8 mL) was dissolved in 80 mL of diethyl ether. After cooling to -15 C, a previously prepared Grignard reagent was added dropwise through a cannula. Slowly raised to room temperature and stirred for 12 hours. The resulting white solid was washed with pentane and the filtrate was concentrated under reduced pressure to give 14.6 g of the title compound.

The synthetic route of 19752-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dae Joo Electronic Materials Co., Ltd.; Jeon Yeong-min; Park Jeong-gyu; Lee Hyeon-seok; Kim Min-yeong; (50 pag.)KR2019/106313; (2019); A;,
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, Application In Synthesis of 3-Bromo-4-fluorochlorobenzene

2-Bromo-6-chloro-3-fluoro-benzaldehyde: To a -78 C. solution of 2-Bromo-4-chloro-1-fluoro-benzene (2.90 g, 13.9 mmol) in 30 mL tetrahydrofuran under an atmosphere of nitrogen was added lithium diisopropylamide solution (1.8M in tetrahydrofuran/heptane/ethylbenzene, 10.0 mL, 18.0 mmol) at such a rate that the internal reaction temperature did not exceed -69 C. After 1 hour at -78 C., dimethylformamide (1.39 mL, 18.0 mmol) was added at such a rate that the internal temperature did not exceed -69 C. After 30 minutes at -78 C., the reaction was quenched with saturated aqueous ammonium hydroxide solution. The resulting mixture was extracted with diethyl ether. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, concentrated in vacuo, and purified by flash chromatography (gradient elution with 0 to 5% ethylacetate/hexanes) to yield 2-Bromo-6-chloro-3-fluoro-benzaldehyde (440 mg, 1.85 mmol). MS (ESI) 236.9 (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; Berthel, Steven; Firooznia, Fariborz; Fishlock, Daniel; Hong, Jun-Bae; Lou, Yan; Lucas, Matthew; Owens, Timothy D.; Sarma, Keshab; Sweeney, Zachary Kevin; Taygerly, Joshua Paul Gergely; US2010/222325; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics