Tag: M.W=200-300

698-19-1, name is 1-(2-Bromophenyl)-N-methylmethanamine, belongs to bromides-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. Product Details of 698-19-1

General procedure: To an oven dried Schlenk tube, were added amine 2 (1 mmol) and alkyl (ethyl or methyl or tert-butyl) acrylate (5 mmol) at room temperature under nitrogen atmosphere. The reaction mixture was stirred at 110 C in an oil bath, for 24 h (in case of methyl as well as ethyl acrylates) and for 48 h (in case of tert-butyl acrylate). Progress of the Michael addition was monitored by TLC. The reaction mixture was allowed to attain room temperature, and excess of alkyl acrylate was removed under vacuum (10-2 mbar). To the resultant reaction intermediate (i.e., Michael addition product 3) at room temperature, were added Pd(OAc)2 (10 mol %), PPh3 (20 mol %), and Cs2CO3 (2 mmol) followed by toluene (3 mL) under nitrogen atmosphere. The reaction mixture was then allowed to stir at 80 C for 24 h (in case of 4a-c and 4f), 36 h (in case of 4d, 4e, 4g, 4i, 4j and 4l-n), and 48 h (in case of 4h and 4k) in an oil bath and the progress was monitored by TLC. The mixture was cooled to room temperature, treated with aqueous NH4Cl solution and then extracted with ethyl acetate (3×15 mL). The organic layer was washed with saturated NaCl solution, dried (Na2SO4), and filtered. Evaporation of the solvent under reduced pressure and purification of the crude material by silica gel column chromatography (petroleum ether/ethyl acetate) furnished the tetrahydroisoquinoline 4 (70-85%).

The synthetic route of 698-19-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reddy, Alavala Gopi Krishna; Satyanarayana, Gedu; Tetrahedron; vol. 68; 38; (2012); p. 8003 – 8010;,
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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. 418762-26-2, name is 4-Bromo-2-fluoro-5-methylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 418762-26-2

To a stirred solution of 4-(2-(benzyloxy)ethoxy)-l-methyl-lH-pyrazole-5-carbonyl chloride (0.9 g, 3.05 mmol, 1 equiv) and 4-bromo-2-fluoro-5-methylaniline (0.6 g, 3.05 mmol, 1 equiv) in DCM was added Et3N (0.5 g, 4.58 mmol, 1.5 equiv) at 0 C under nitrogen atmosphere. The resulting solution was stirred for 30 min. The reaction was quenched with water at room temperature. The aqueous layer was extracted with CH2CI2 and the organic layer was concentrated under reduced pressure to give the title compound (1 g, 70.84%) as a white solid. LC-MS: (ES, m/z): [M+H]+ 462.

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; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; BECK, Hilary, Plake; DILLON, Michael, Patrick; GONZALEZ-LOPEZ, Marcos; SUTTON, James, Clifford, Jr.; (248 pag.)WO2019/156987; (2019); A1;,
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Synthetic Route of 185122-74-1, 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 185122-74-1 as follows.

At 0 0C and under protective atmosphere, a solution of 2-propanesulfonyl chloride (1 1.87 mL, 121 mmol) in DCM (121 mL) was added gradually to a solution of 5-bromo-2,3- dihydro-7/-/-inden-1 -amine (12.8 g, 60.4 mmol) and 1 ,8-diazabicyclo[5.4.0]undec-7-ene (4.83 mL, 32.1 mmol) in dichloromethane (300 mL). The reaction was stirred at rt overnight. The reaction mixture was washed with 1 N KHSO4 (1x) and sat NaHCOs (2x) before being dried on IS^SO4 and solvent evaporated in vacuo to afford a green oil. Purification by column chromatography (25% EtOAc in hept) afforded the title compound as a white solid (6.0 g, 18.9 mmol, 31 %). MS (ESI) : m/z [M – H]”317.0.

According to the analysis of related databases, 185122-74-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N.V. ORGANON; WO2009/147167; (2009); A1;,
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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. 112279-72-8, name is 4-Bromo-2,3-difluoroaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 112279-72-8

Benzyl chloroformate (1.1 mL, 7.5 mmol) was added dropwise with stirring to the Intermediate 52 (1.0 g, 4.8 mmol) in 10% aq. NaOH (15 mL)) and THF (30 mL) at ca. 0 C. The reaction mixture was stirred at r.t. for ca. 6 h. The reaction was quenched with 10% NH4Cl solution and extracted with DCM (2×50 mL). Combined organic layers were washed with brine, dried (Na2SO4), and concentrated under vacuum. The residue was purified by preparative TLC (10% ethyl acetate/petroleum ether) to give the product as a white solid. 1H NMR (400 MHz, CDCl3): 7.88 (m, 1H); 7.40 (m, 5H); 6.90 (m, 1H); 5.25 (s, 2H).

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; Gordeev, Mikhail Fedorovich; US2009/48305; (2009); A1;,
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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 16518-62-0 as follows. Safety of 3-Bromo-N,N-dimethylaniline

N,N-Diallyl-3-bromo-4-(2-bromo-4-(dimethylamino)benzyl)aniline (7) A solution of 3-bromo-N,N-dimethylaniline (7.54 g, 37.7 mmol) and 3-bromo-N,N-diallylaniline (9.51 g, 37.7 mmol) in glacial AcOH (250 mL) was treated with a 37 wt. percent solution of formaldehyde in H2O (30 mL). The resultant suspension was stirred at 80° C. for 2 h. After cooling to room temperature, the volatiles were removed under reduced pressure. The syrupy residue was dissolved in CH2Cl2 (100 mL), washed with sat. Na2CO3 (100 mL*2) and brine (100 mL), dried (Na2SO4), and concentrated under reduced pressure to afford a light brown syrup (16.9 g). 1H NMR analysis indicates that this mixture consists of approximately 30percent the desired product. The inseparable mixture was used in the subsequent step without further purification. 1H NMR (400 MHz, CDCl3): delta 6.91 (d, J=2.8 Hz, 2H), 6.82 (d, J=8.1 Hz, 2H), 6.55 (dd, J=2.8, 8.8 Hz, 2H), 5.78-5.87 (m, 2H), 5.14-5.20 (m, 4H), 3.98 (s, 2H), 3.85-3.87 (m, 4H), 3.15 (s, 6H).

According to the analysis of related databases, 16518-62-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHANG, Christopher J.; VAN DE BITTNER, Genevieve V.; HIRAYAMA, Tasuku; CHAN, Jefferson; US2014/51863; (2014); A1;,
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These common heterocyclic compound, 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, 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. Product Details of 327-52-6

To a dryflask (equipped with a magnetic stirrer and a rubber septum) filledwith argon, 1-bromo-2,4,5-trifluorobenzene 45 (4.39 mL, 37.5 mol)and anhydrous THF (10.6 mL) were added and cooled to 20 C;2 M solution of iPrMgCl in THF (22.5 mL) was slowly added tothe reaction mixture, the reaction temperature was adjusted to10 C and the mixture was stirred for one hour until theGrignard exchange reaction was completed. The resulting solutionof 46 was added dropwise to the solution of ethyl 4-iodobenzoate38 (0.50 mL, 3.0 mmol), tetrakis(triphenylphosphine)palladium(299 mg, 0.15 mmol) and HMTA (21 mg, 0.15 mmol) in anhydrousTHF (20 mL) at 0 C. The reaction mixture was maintained at 0 Cfor one hour and then stirred overnight at room temperature.The solvent was removed by evaporation and the residue was purifiedby column chromatography using diethylether/hexane (1:10)as an eluent to obtain 0.70 g (83%) of compound 47 as white crystals.Mp 73-75 C; 1H NMR (400 MHz, CDCl3): d (ppm) 1.42 (t,J = 7.2 Hz, 3H, CH3), 4.41 (q, J = 7.2 Hz, 2H, CH2), 7.02-7.08 (m,1H, Ar-H), 7.25-7.32 (m, 1H, Ar-H), 7.56 (d, J = 8.8 Hz, 2H, Ar-H),8.12 (d, J = 8.8 Hz, 2H, Ar-H); 13C NMR (100 MHz, DMSO-d6): d(ppm) 14.08, 60.88, 106.80 (dd, 1H, 2JC,F = 21.2 Hz, 2JC,F0 = 29.7 Hz),118.51 (dd, 1H, 3JC,F = 4.2 Hz, 2JC,F = 19.9 Hz), 124.00 (ddd,3JC,F = 4.5 Hz, 3JC,F = 5.7 Hz, 2JC,F = 15.7 Hz), 129.14 (d, 1H, 3JC,F =3.2 Hz), 129.35, 129.54, 137.71, 146.53 (ddd, 4JC,F = 3.3 Hz,2JC,F = 13.6 Hz, 1JC,F = 241,4 Hz), 149.08 (dt, 3JC,F = 13.2 Hz, 2JC,F =13.6 Hz, 1JC,F = 248.5 Hz), 154.39 (ddd, 4JC,F = 1.2 Hz, 3JC,F = 9.8 Hz,1JC,F = 245,1 Hz), 165.28; HR-MS (ESI): m/z calcd for C15H12O2F3 [M+H]+ 281.0789, found: 281.0787; HPLC tR = 13.669 min (97.2%,method 2).

The synthetic route of 1-Bromo-2,4,5-trifluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Berne, Sabina; Kova?i?, Lidija; Sova, Matej; Kra?evec, Nada; Gobec, Stanislav; Kri?aj, Igor; Komel, Radovan; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4264 – 4276;,
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Application of 40161-54-4, 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. 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate M: 5-(2-Fluoro-4-(trifluoromethyl)phenyl)-l,2,3,4- tetrahydroisoquinoline hydrochloride A solution of Pd(PPh3)4 (Strem Chemicals Inc., Newburyport, MA, 0.643 g, 0.557 mmol), l-bromo-2-fluoro-4-(trifluoromethyl)benzene (1.353 g, 5.57 mmol), tert-butyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline- 2(lH)-carboxylate (ASW Medchem, Brunswick, NJ, 2.000 g, 5.57 mmol), and potassium carbonate (3.08 g, 22.27 mmol) in 12 mL dioxane and 6 mL water was heated to 120 C for 3 days. The reaction mixture was diluted with diethyl ether, washed with water, the organics dried over MgS04 and concentrated to provide tert- butyl 5-(2-fluoro-4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(lH)- carboxylate. The resulting residue was dissolved in 10 mL THF and was treated with HCI 4 N in dioxane (9.74 ml, 39.0 mmol), and allowed to stir at room temperature overnight. The reaction mixture was diluted with diethyl ether/heptane, and the resulting solid was filtered and dried yielding 5-(2-fluoro-4-(trifluoromethyl)phenyl)- 1,2,3,4-tetrahydroisoquinoline hydrochloride (1.930 g, 5.82 mmol). [M+H]+ = 296.1

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AMGEN INC.; DINEEN, Thomas; KREIMAN, Charles; WEISS, Matthew; GEUNS-MEYER, Stephanie; WO2013/134518; (2013); A1;,
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Related Products of 51776-71-7, A common heterocyclic compound, 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, molecular formula is C7H5BrF2, 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: Under an argon atmosphere, degassed CCl4 (0.35 M) was addedto a round bottom flask containing the corresponding difluoromethyl arene (1.0 equiv.) and N-Bromosuccinimide (1.7 equiv.). The reaction mixture was irradiated by the light of a 120 W sun lamp (approx. 12 cm distance between lamp and reaction flask) for 1-30 days before being quenched with Na2S2O3 (sat. aq.) and extracted with CH2Cl2 (330 mL). The combined organic layers were washed with brine, dried over MgSO4 and the solvent was removed under reduced pressure. Purification by column chromatography afforded the desired bromodifluoromethyl arenes. 1-Bromo-4-(bromodifluoromethyl)benzene (3c). Following the general procedure B from 4-bromobenzaldehyde with a reaction time of 2 days. Purification by column chromatography (SiO2; pentane/Et2O 100:1) afforded 1-Bromo-4-(difluoromethyl)benzene as a colorless oil (1.05 g, 81%). 1H NMR (400 MHz,CDCl3, TMS): d = 7.62-7.58 (m, 2H), 7.41-7.36 (m, 2H), 6.61 (t, J(H,F) = 56.3 Hz, 1H). 13C NMR (100 MHz, CDCl3, TMS): d = 133.4 (t, J(C,F) = 22.8 Hz), 132.1, 127.4 (t, J(C,F) = 6.0 Hz), 125.3 (t, J(C,F) = 2.5 Hz),114.3 (t, J(C,F) = 239.2 Hz). 19F NMR (377 MHz, CDCl3): d =111.10(d, J(F,H) = 56.3 Hz). (EI) m/z (rel intens) 207.89 (M+, 81Br, 100),205.98 (M+, 79Br, 93), 127.23 (M+-Br, 49). From 1-Bromo-4-(difluoromethyl)benzene with a reaction time of 9 days. Purification by column chromatography (SiO2; pentane) afforded the title compound as a colorless oil (745 mg, 82%). 1H NMR (400 MHz,CDCl3, TMS): d = 7.62-7.58 (m, 2H), 7.50-7.46 (m, 2H). 13C NMR(100 MHz, CDCl3, TMS): d = 137.3 (t, J(C,F) = 24.2 Hz), 132.1, 126.1 (t, J(C,F) = 5.1 Hz), 126.0 (t, J(C,F) = 1.7 Hz), 117.8 (t, J(C,F) = 303.7 Hz). 19FNMR (377 MHz, CDCl3): d =44.05 (s). (EI) m/z (rel intens) 207.19(M+79Br-Br, 96), 205.17 (M+81Br-Br, 100), 126.23 (M+-Br2, 47).

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; Bermejo Gome, Antonio; Gonzalez, Miguel A. Cortes; Luebcke, Marvin; Johansson, Magnus J.; Schou, Magnus; Szabo, Kalman J.; Journal of Fluorine Chemistry; vol. 194; (2017); p. 51 – 57;,
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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. 154264-95-6, name is 7-Bromo-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine, A new synthetic method of this compound is introduced below., Safety of 7-Bromo-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine

n-Butyl lithium (1.6M in hexane, 6.85 mL, 11.0 mmol) was added dropwise to a stirred solution of 7-bromo-4-methyl-3,4-dihydro-2H-l,4-benzoxazine (CAS: 154264-95-6; 2.00 g, 8.77 mmol) in Me-THF (30 mL) under N2 atmosphere at -78 C. The reaction mixture was stirred at -78 C for 30 min and a solution of N-methoxy-N- methylacetamide (CAS:78l9l-00-l; 1.81 g, 17.5 mmol) in Me-THF (10 mL) was added dropwise. The reaction mixture was stirred at -78 C for 1 h and at room temperature for 1 h. The reaction was quenched with NH4Cl (sat.) and extracted with EtOAc. The organic layer was dried (Na2S04), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (silica, EtOAc in heptane, gradient from 0/100 to 30/70). The desired fractions were collected and concentrated in vacuo to afford intermediate 54 (818 mg, 49%) as a yellow 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; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; MARTINEZ-VITURRO, Carlos Manuel; DELGADO-JIMENEZ, Francisca; CONDE-CEIDE, Susana; VEGA RAMIRO, Juan, Antonio; (178 pag.)WO2019/243527; (2019); A1;,
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Related Products of 156682-52-9, 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 156682-52-9 as follows.

A solution of intermediate 4 (5 g, 18.1 mmol), 1,4-dibromo-2,3-difluorobenzene (2.4 g, 9.0 mmol), tetrakis (triphenylphosphine) palladium (0) mmol) is added to a mixed solvent of tetrahydrofuran (60 ml) and potassium carbonate 2M solution (20 ml) and refluxed for 24 hours. After the reaction was completed, the reaction solution was extracted with methylene chloride, and then subjected to column chromatography using a methylene chloride / hexane mixed solvent as a developing solvent to obtain 4.3 g of Intermediate 5.

According to the analysis of related databases, 156682-52-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LG Chem, Ltd.; Dankook University Cheonan Campus Industry-Academic Cooperation Foundation; Gu Gi-dong; Lee Gi-gon; Keum Su-jeong; Kim Gong-gyeom; Lee U-cheol; Lee Chil-won; Cha Jae-ryeong; Joo Yun-seok; (30 pag.)KR2018/106234; (2018); A;,
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