Tag: M.W=200-300

Some common heterocyclic compound, 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, molecular formula is C7H5BrF2, 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. category: bromides-buliding-blocks

Example 33A 1-Bromo-4-[bromo(difluoro)methyl]benzene With exclusion of oxygen, a solution of 14.0 g (67.63 mmol) of 1-bromo-4-(difluoromethyl)benzene [CAS 51776-71-7] and 25.3 g (142 mmol) of N-bromosuccinimide (NBS) in 190 ml of tetrachloromethane is irradiated with a sun lamp. During this, the solvent reaches its boiling point. It is irradiated under reflux for 24 hours. The mixture is then allowed to cool to room temperature and precipitated succinimide is filtered off. The filtrate is again mixed with 25 g of NBS and irradiated once more with exclusion of oxygen under reflux for 24 hours. Cooling is followed by filtration again, and the filtrate is concentrated to dryness. 18 g of an orange-colored oil are obtained as crude product, which is purified further by vacuum distillation at 13 mmHg. 12.7 g (44.4 mmol, 66% yield) of a colorless oil are obtained. Boiling point (13 mmHg): 90-92 C. 1H-NMR (300 MHz, DMSO-d6, o/ppm): 7.79 (2H, d), 7.63 (2H, d). MS (ESI): 205/207 (M-Br+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51776-71-7, its application will become more common.

Reference:
Patent; BAYER HEALTHCARE AG; US2009/227640; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 626-40-4, name is 3,5-Dibromoaniline, belongs to bromides-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 626-40-4, Quality Control of 3,5-Dibromoaniline

The 5.018 (0.02 muM) 3, 5 – dibromoaniline and 7.149 g (0.05 muM) (5 – aminothiophen – 2 – yl) boronic acid is added to a 500 ml three-neck bottle in, adding 400 ml tetrahydrofuran (THF), then adding 2 mol/L potassium carbonate solution of 75 ml, and add 0.5 ml of aliquat 336, magnetic stirring and open the argon gas, oil bath is heated to 75 C after, adding 0.020 g […] palladium, reflux reaction 24 h, the reaction liquid is poured into the water in the, a large amount of precipitate out. For funnel, evaporating the solvent under reduced pressure. The product in order to dichloromethane: hexane=3:1 ([…]) as the mobile phase silica gel as stationary phase makes the column chromatographic purification, collecting products and turns on lathe does, in 90 C drying in vacuum 24 h, to obtain the target product 4.311 g, yield is 75%.

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, 3,5-Dibromoaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hunan University of Technology; Ding Qian; Tan Jinghua; Liu Yiwu; Fu Hao; (20 pag.)CN109053466; (2018); A;,
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Application of 67567-26-4, A common heterocyclic compound, 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, molecular formula is C6H4BrF2N, 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.

4-Bromo-2,6-difluoroaniline (5.00 g, 24.0 mmol, 1.00 equiv) and copper(I) cyanide (6.45 g, 72.0 mmol, 3.00 equiv) were suspended in 50 mL DMF and heated at 120 C for 24 h. After cooling to room temperature, the mixture was poured into an aqueous solution of ammonia (12%, v%, 250 mL). The mixture was then filtered and the precipitate was washed with EtOAc (500 mL). The organic phases were combined and washed with the ammonia solution (500 mL), distilled water (500 mL), brine (500 mL) and dried over anhydrous MgSO4. Solvents were removed under reduced pressure. The crude was purified by flash column chromatography (CH2Cl2/n-pentane, 2:1, v/v) to yield the desired compound (1.88 g, 12.2 mmol, 51%) as a white solid.

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; Zhang, Lei; Linden, Greta; Vazquez, Olalla; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 2500 – 2508;,
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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. 65185-58-2, name is 2-Bromophenethylamine, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

4m was then obtained by following the general procedure. A solution of compound 3 (160 mg, 0.81 mmol) in n-BuOH (6 mL) was treated with DIEA (114 mg, 0.89 mmol) and 2-chlorophenethylamine (162 mg, 0.81 mmol). Compound 4m was purified from this crude material by column chromatography (silicagel, n-hexane/EtOAc=3:1) (118.6 mg, 40.1%). 1H-NMR (400 MHz, DMSO-d6) delta 8.88 (t, J=5.2 Hz, 1H, N-H), 8.21 (d, J=7.6 Hz, 1H), 7.79 (t, J=8.4 Hz, 1H), 7.58 (t, J=15.6 Hz, 2H), 7.52 (t, J=8.4 Hz, 1H), 7.40-7.26 (m, 2H), 7.16 (td, J=8.6, 2.0 Hz, 1H), 3.70-3.60 (m, 2H, -CH2-), 3.11 (t, J=7.6 Hz, 2H, -CH2-). 13C-NMR (100 MHz, DMSO-d6) delta161.6, 157.4, 150.7, 138.8, 134.1, 133.0, 131.6, 129.0, 128.3, 127.1, 126.6, 124.5, 123.5, 114.0, 41.2, 34.8; LRMS (ESI) m/z: 363.2 ([M+H]+).

The synthetic route of 65185-58-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Board of Regents of the University of Oklahoma; Wang, Weidong; Lee, Jae Wook; (35 pag.)US2019/47988; (2019); A1;,
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Application of 176317-02-5,Some common heterocyclic compound, 176317-02-5, name is 1-Bromo-2,3,4-trifluorobenzene, molecular formula is C6H2BrF3, 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.

Step 1 : tert-butyl 4-(2,3,4-trifluorophenyl)piperazine-l-carboxylate (1053) [00366] A mixture of A24-1C (200 mg, 0.95 mmol, 1 12.4 uL, 1.0 eq), A24-1D (21 1.9 mg, (1054) 1.1 mmol, 1.2 eq), Pd2(dba)3 (86.8 mg, 94.8 umol, 0.1 eq), BINAP (118. 1 mg, 0. 19 mmol, 0.2 eq) and f-BuONa (136.7 mg, 1.4 mmol, 1.5 eq) in toluene (5 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 100 C for 16 hour under N2 atmosphere. TLC showed Reactant A24-1C was consumed completely and one main new spot was detected. The reaction mixture was concentrated to give a residue. The residue was purified by column chromatography (Petroleum ether/Ethyl acetate= 1 :0-8: 1) to give compound A24-1B (250 mg, 790.3 umol, 83.4% yield) as a yellow oil. NMR (400 MHz, CDC13) delta 6.82 – 6.79 (m, 1H), 6.57 – 6.53 (m, 1H), 3.52 (t, J = 4.8 Hz, 4H), 2.91 (t, J = 4.8 Hz, 4H), 1.41 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2,3,4-trifluorobenzene, its application will become more common.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; LIN, Tracy Tzu-Ling Tang; KONRADI, Andrei W.; VACCA, Joseph; SHEN, Wang; COBURN, Craig; (231 pag.)WO2017/58716; (2017); A1;,
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Application of 337915-79-4,Some common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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: HATU (4.89 g, 12.9 mmol) was added to a solution of the intermediate 4-bromo-N2-ethylbenzene-1,2-diamine, DIPEA (6.40 mL, 36.7 mmol), and cyclopropanecarboxylic acid (0.98 mL, 12.2 mmol) in DMF (40 mL), and the mixture was stirred at rt for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was dissolved in AcOH (40 mL) and the mixture was stirred at 80 C for 1 h. After concentration of the mixture, the residue was neutralized with satd NaHCO3 solution and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by column chromatography (silica gel, hexane/EtOAc = 100/0 to 0/100) to give the title compound (1.2 g, 37%) as a pale yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-N1-methylbenzene-1,2-diamine, its application will become more common.

Reference:
Article; Igawa, Hideyuki; Takahashi, Masashi; Shirasaki, Mikio; Kakegawa, Keiko; Kina, Asato; Ikoma, Minoru; Aida, Jumpei; Yasuma, Tsuneo; Okuda, Shoki; Kawata, Yayoi; Noguchi, Toshihiro; Yamamoto, Syunsuke; Fujioka, Yasushi; Kundu, Mrinalkanti; Khamrai, Uttam; Nakayama, Masaharu; Nagisa, Yasutaka; Kasai, Shizuo; Maekawa, Tsuyoshi; Bioorganic and Medicinal Chemistry; vol. 24; 11; (2016); p. 2486 – 2503;,
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Electric Literature of 103273-01-4, A common heterocyclic compound, 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, molecular formula is C10H14BrN, 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.

To a suspension of 4-trifluoromethylbenzoic acid (420 mg, 2.2 mmol) in dichloromethane (5 mL) was added N,N-dimethylformamide (1 drop) followed by oxalyl chloride (225 muL, 2.6 mmol) at 0 C. The mixture was warmed to room temperature and stirred for 4 hours before the volatile components were removed under a stream of nitrogen. The crude acid chloride was taken up in dichloromethane (2 mL) and added to a cooled solution of the aniline 39 (500 mg, 2.2 mmol) in dichloromethane (10 mL) and the mixture was stirred for 16 hours at room temperature. The reaction mixture was diluted with dichloromethane (20 mL), washed with saturated aqueous sodium hydrogen carbonate solution (2 x 20 mL) and saturated aqueous ammonium chloride solution (2 x 20 mL), dried over anhydrous magnesium sulfate and concentrated. The crude solid was purified by flash column chromatography using ethyl acetate, hexane (1:49 to 1:24) as an eluent and recrystallisation from isopropyl alcohol, water to obtain the title compound (660 mg, 75%) as a white solid, mp: 151.7-152.7 C; Rf: 0.63 (1:9 ethyl acetate, hexane); IR (vmax (film)): 3343, 2966, 1660, 1509, 1318, 1111, 1065 cm-1; 1H NMR (300 MHz, CDCl3): delta 1.31 (9H, s), 7.41 (1H, s), 7.79 (2H, d, J = 8.0 Hz), 8.04 (2H, d, J = 8.0 Hz), 8.31-8.45 (2H, m) ppm; 13C NMR (75 MHz, CDCl3): delta 31.4, 34.8, 114.1, 121.7, 123.6 (q, J = 270.0 Hz), 125.8, 126.2 (q, J = 3.6 Hz), 127.7, 129.4, 132.9, 133.2 (q, J = 31.2 Hz), 138.1, 149.6, 164.0 ppm; 19F NMR (282 MHz, CDCl3): delta -63.0 ppm; LRMS (+ESI) m/z: 422.0/424.0 ([M+Na]+ 100%); HRMS (ESI)+ Cald for C18H17BrF3NO [M+Na]+: 422.03378/424.03174, found 422.03396/424.03190.

The synthetic route of 103273-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moir, Michael; Boyd, Rochelle; Gunosewoyo, Hendra; Montgomery, Andrew P.; Connor, Mark; Kassiou, Michael; Tetrahedron Letters; vol. 60; 36; (2019);,
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Electric Literature of 698-00-0, 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. 698-00-0, name is 2-Bromo-N,N-dimethylaniline, This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of 2-(di-l-adamantylphosphino)-N^V-dimethylaniline (L2).[0287] Pd(OAc)2 (6.3 mg, 0.028 mmol) was added to a glass vial and dissolved in toluene (2 mL). This solution was then transferred to a vial containing DiPPF(l,l’-bis(diisopropylphosphino)ferrocene; 14.2 mg, 0.034 mmol) and was left to stir for 10 minutes. To a separate glass vial containing NaOtBu (192 mg, 2.0 mmol) was added a solution of (l-adamantyl)2PH (410 mg, 1.36 mmol) in 2 mL toluene, followed by2-bromo-NjV-dimethylaniline (230 L, 1.4 mmol), and the Pd(OAc)2/DiPPF solution, after which the vial was sealed with a cap containing a PTFE septum. The mixture was stirred for 20 h at 110 C, at which point the reaction was deemed complete on the basis of 31P NMR data obtained from an aliquot of the reaction mixture. The reaction mixture was then allowed to cool and was passed through a plug of silica, followed by washing of the plug with 40 mL of CH2C12. The combined eluent was collected and the solvent was removed in vacuo. The resulting pale orange solid was washed with cold hexanes (2 x 4 mL). Removal of volatile materials in vacuo yielded the product as an off-white powder (0.424 g, 1.01 mmol; 74 % yield). 1H NMR (CDC13): delta 7.71 (m, 1H, Ar-H), 7.32 (m, 1H, Ar-H), 7.20 (m, 1H, Ar-H), 7.05 (m, 1H, Ar-H), 2.71 (s, 6H, N(CH3)2), 2.01-1.89 (m, 18Eta, 1-Ad), 1.67 (s, 12Eta, 1-Ad). 13C{ ‘H} NMR (CDCI3): delta 161.6 (d, JPC = 21.6 Hz, Cquat), 137.4 (d, JPC = 3.3 Hz), 131.1 (d, JPC = 22.9 Hz, Cquat), 129.6, 122.2, 120.6 (d, Jpc = 3.9 Hz), 46.1 (d, Jpc = 4.2 Hz, N(CH3)2), 41.8 (d, Jpc = 13.0 Hz, CH2), 37.1 (CH2), 29.0 (d, /PC = 8.6 Hz, CH). 31P{ 1H} NMR (CDC13): delta 20.1. HRMS (ESI/[M+H]+) calcd. for C28H40N1P1: 422.2971. Found: 422.2978. Anal. Calcd for C^fttoPiNi: C 79.77; H 9.56; N 3.32. Found: C 79.47; H 9.46; N 3.31.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-N,N-dimethylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DALHOUSIE UNIVERSITY; LUNDGREN, Rylan, J.; STRADIOTTO, Mark; WO2012/68335; (2012); A2;,
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Synthetic Route of 1435-51-4, These common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-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.

l,3-Dibromo-5-fluorobenzene (10.2 g, 40.7 mmol) was dissolved in 1,4- dioxane. Pyridine-4-ylboronic acid (5 g, 40.7 mmol), tetrakis(triphenylphosphine)- palladium(O) (462 mg, 0.41 mmol), and K2CO3 (11.22 g, 81 mmol) were added, and the mixture was heated at 900C for 4 h. The reaction was diluted with EtOAc, washed with aq. NaHCO3 and dried and removed. Purification via column chromatography afforded 4-(3-bromo-5-fluorophenyl)pyridine (6 g, 59%). 1H NMR (400 MHz, CDCl3): delta 8.73 (d, IH), 8.58 (d, IH), 7.77 (dd, IH), 7.45 (s, IH), 7.34-7.31 (m, IH), 7.22 (t, IH), 7.18- 7.15 (m, IH).

Statistics shows that 1,3-Dibromo-5-fluorobenzene is playing an increasingly important role. we look forward to future research findings about 1435-51-4.

Reference:
Patent; SEPRACOR INC.; BURDI, Douglas; SPEAR, Kerry, L.; HARDY, Larry, Wendell; WO2010/114971; (2010); A1;,
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Synthetic Route of 40161-54-4, These common heterocyclic compound, 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, 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.

(1) 1-[2-Fluoro-4-(trifluoromethyl)phenyl]butan-1-one To a solution of 1-bromo-2-fluoro-4-(trifluoromethyl)benzene (0.30mL, 2.1mmol) in THF (6mL) was added dropwise 1.5M butyllithium in THF (1.65 mL) at -78C. The mixture was stirred at -78C for 15 minutes, to which was added a solution of butyraldehyde (0.18 mL, 2.5 mmol) in THF (2 ml) at -78C. After stirring at -78C for 30 minutes, the mixture was treated with acetic acid (1 mL)/THF (2 mL), and then followed by water at room temperature. The organic layer was separated, and the aqueous layer was extracted with ether. The combined organic layers were washed with saturated brine. After drying over anhydrous sodium sulfate, the solvent was removed under reduced pressure to give 1-[2-fluoro-4-(trifluoromethyl)-phenyl]butanol.

Statistics shows that 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene is playing an increasingly important role. we look forward to future research findings about 40161-54-4.

Reference:
Patent; Nippon Chemiphar Co., Ltd.; EP2277874; (2011); A1;,
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