Month: June 2021

Reference of 67567-26-4, The chemical industry reduces the impact on the environment during synthesis 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, I believe this compound will play a more active role in future production and life.

A solution of 4-bromo-2,6-difluoroaniline (15g) in dry DMF (180ml) was degassed for SOmin. Water (42ml) was added and the solution was further degassed for 10min. n-Butyl vinyl ether (46.60ml), 1,3-bis(diphenylphosphiho)propane (1.96g), potassium carbonate (11.76g), and palladium (II) acetate (0.48g) were added and the mixture was stirred at 80C under nitrogen for 6h and then at ambient temperature for 18h. The5 mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The separated organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was treated with MeCN (100ml), water (100ml) and formic acid (2ml) and stirred at ambient temperature for 45min. The mixture was concentrated under reduced pressure and partitioned between) DCM and saturated aqueous sodium bicarbonate solution. The separated organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash vacuum chromatography (silica, eluting withether). Trituration with cyclohexane afforded a solid which was filtered and dried undervacuum at ambient temperature to give the title compound (10.47g) as a cream solid.Mass spectrum: Found MM* 172H.p.l.c. Rt 2.27 min

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, 4-Bromo-2,6-difluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/110997; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 18648-66-3, The chemical industry reduces the impact on the environment during synthesis 18648-66-3, name is 2-(4-Bromophenyl)-1,1-diphenylethylene, I believe this compound will play a more active role in future production and life.

A flask was charged with a mixture of 3-(4-vinylphenyl)-9-ethylcarbazole (1, 0.3 g, 1.01 mmol), 2-(4-bromophenyl)-1,1-diphenylethylene (triPE, 0.28 g, 0.84 mmol), palladium acetate(Pd(OAc)2, 2.3 mg, 0.01 mmol), P(o-tolyl)3 (15 mg, 0.05 mmol),dimethylformamide (8 mL) and trimethylamine (3 mL). The flaskwas degassed and purged with argon. The reaction mixture washeated at 90 C for 4 h under argon atmosphere. Then, it wasfiltered, and was purified by column chromatography using hexane/ethyl acetate (50/1) as an eluent. The target product wasrecrystallized from the eluent mixture of solvents. The yield ofyellow crystals was 43% (0.2 g). Mp 219-220 C. MS (APCI, 20V),m/z(%): 553 ([MH], 100). 1H NMR (400 MHz, CDCl3, d, ppm): 1.49(t, J 7.2 Hz, 3H, CH3), 4.40 (q, J 7.2 Hz, 2H, NCH2), 7.01 (s, 1H, CH),7.07 (d, J 8.4 Hz, 2H, Ar), 7.13 (d, J 6.3 Hz, 2H, Ar), 7.27e7.53 (m,16H, Ar, 2CH), 7.62 (d, J 8.3 Hz, 2H, Ar), 7.73e7.78 (m, 3H, Ar), 8.20(d, J 8.4 Hz, 1H, Ar), 8.34 (s, 1H, Ar). 13C NMR (100 MHz, CDCl3, d,ppm): 13.9 (CH3), 37.7 (CH2), 108.6, 108.7, 118.7, 119.0, 120.5, 123.1,123.5,125.0,125.9,126.1,127.0,127.4,127.5,127.6,127.8,127.9,128.2,128.8, 129.9, 130.4, 131.7, 135.5, 135.9, 136.8, 139.5, 140.4, 141.4,142.6, 143.4. IR. nmax in cm1 (KBr): (CeH Ar) 3048, 3021; (CeH)2970, 2929; (C]C Ar) 1597, 1456, 1443; (CeN) 1233; (trans, CH]CH) 978; (CeH, Ar) 801, 761, 701. Elemental analysis. Calcd. forC42H33N (%): C 91.43, H 6.03, N 2.54. Found (%): C 91.36, H 6.09, N2.64.

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-(4-Bromophenyl)-1,1-diphenylethylene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Tomkeviciene; Sutaite; Volyniuk; Kostiv; Simkus; Mimaite; Grazulevicius; Dyes and Pigments; vol. 140; (2017); p. 363 – 374;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 2789-89-1, 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. 2789-89-1 name is 1,2-Bis(4-bromophenyl)ethyne, 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.

General procedure: To an oven-dried screwed vial were added substituted 2-oxo-2-phenylacetic acid (0.1mmol), substituted alkyne (0.11mmol), [IrCp*Cl2]2 (0.01mmol, 7.97mg), (CH3OC6H4)3P (0.01mmol, 3.52mg), AgSbF6 (0.01mmol, 3.44mg), Cu(OAc)2 (0.02mmol, 3.99mg), and toluene (1mL). The mixture was vigorously stirred at 120C under air to the end of the reaction. Organic solvents were removed in vacuo, and then the residue was purified by a silica gel column chromatography to give the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2-Bis(4-bromophenyl)ethyne, and friends who are interested can also refer to it.

Reference:
Article; Yu, Xiaobo; Geng, Shudong; Liu, Guanchen; Guo, Weijie; Wang, Jianhui; Journal of Organometallic Chemistry; vol. 879; (2019); p. 139 – 143;,
Bromide – Wikipedia,
bromide – Wiktionary

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;,
Bromide – Wikipedia,
bromide – Wiktionary

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;,
Bromide – Wikipedia,
bromide – Wiktionary

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;,
Bromide – Wikipedia,
bromide – Wiktionary

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;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 2695-48-9,Some common heterocyclic compound, 2695-48-9, name is 8-Bromo-1-octene, molecular formula is C8H15Br, 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 stirred solution of 4,5-diphenyl-2-((phenylsulfonyl)methyl)oxazole419 (2.7 g, 0.007 moles, 1.0 equiv) in dry THF (50 mL) was added potassium tert-butoxide (0.97 g, 0.003 mol, 1.2 equiv) under a nitrogen atmosphere at 0-5C and stirred was continued for 30 min. To this solution was added dropwise 8-bromo-1-octene (1.51 g, 0.008 mol, 1.1 equiv). After addition of the bromide, the reaction mixture was allowed to warm to room temperature and then stirred overnight. Water (30 mL) was then added to the reaction mixture followed by extraction with dichloromethane (2 x 25 mL). The organic layers were separated and combined, and the aqueous layer was washed with dichloromethane (2 x 10 mL). All the dichloromethane extracts were combined and dried over anhydrous sodium sulfate. Removal of the drying agent and concentration resulted in a reddish crude residue which was purified by column chromatography (hexane/ethyl acetate, 9:1) to give pure 4,5-diphenyl-2-(1-(phenylsulfonyl)non-8-en-1-yl)oxazole 20 (2.3 g, 66% yield) as athick colorless oil. Rf = 0.44 (hexane/ethyl acetate, 7.5:2.5); FT- IR: 3064, 2932, 2857, 1702, 1447, 1308, 1147, 686 cm-1; 1H NMR (400 MHz, CDCl3): delta 7.78-7.75 (m, 2H), 7.65-7.60 (m, 1H), 7.51-7.46 (m, 6H), 7.37-7.33 (m, 6H), 5.81-5.71 (m, 1H), 4.98-4.89 (m, 2H), 4.50 (dd, J = 10 Hz, 5.2 Hz, 1H), 2.40-2.34 (m, 2H), 2.03-1.98 (m, 2H), 1.40-1.31 (m, 8H) ppm; 13C NMR (175 MHz, CDCl3): delta 154.9, 147.0, 138.9, 137.3, 136.0, 134.0, 131.8, 129.1, 129.0, 128.9, 128.7, 128.5, 128.4, 128.2, 127.9, 126.6, 114.3, 65.9, 33.6, 28.8, 28.64, 28.58, 26.9, 26.4 ppm; HRMS calcd for C30H31NO3S (EI+) 485.2025, Found 485.2025

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 8-Bromo-1-octene, its application will become more common.

Reference:
Article; Patil, Pravin C.; Luzzio, Frederick A.; Tetrahedron Letters; vol. 58; 13; (2017); p. 1280 – 1282;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 43204-63-3, name is Bis(2-Bromoethyl)amine hydrobromide, A new synthetic method of this compound is introduced below., COA of Formula: C4H10Br3N

To a mixture of 5-amino-3,4-dihydroquinolin-2(1H)-one 1(5.00 g, 30.83 mmol), bis(2-bromoethyl)amine hydrobromide(9.05 g, 33.91 mmol) and water (40 mL), a solution of potassiumhydroxide (1.90 g, 33.91 mmol,10 mL)was added dropwise at 80 C.Then the reaction mixture was stirred at 100 C for 3 h. The progressof the reaction was monitored by TLC. After the reaction wascompleted, the reaction mixture was cooled to the room temperature.The mixture was filtered and the filtrate was adjusted toPH 10 with the 10% aqueous solution of potassiumhydroxide. Theresultant solid was filtered, washed with water to afford 6.4 g of 5-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one 2 as a white solid.Yield 61%, m. p. 235e237 C; 1H NMR (300 MHz, DMSO-d6) d: 10.01(s, 1H, quinolin, eCONHe), 7.07 (t, J 7.9 Hz, 1H, quinolin-H7), 6.65(d, J 8.0 Hz, 1H, quinolin-H8), 6.58 (d, J 7.8 Hz, 1H, quinolin-H6),3.94 (s, 1H, NH), 2.82e2.94 (m, 4H, quinolin-H4 and eCH2-),2.67e2.84 (m, 6H, eCH2-), 2.35 (t, J 7.3 Hz, 2H, quinolin-H3); 13CNMR (75 MHz, DMSO-d6) d: 170.59, 150.18, 139.44, 127.33, 117.62,112.55, 110.18, 51.34, 46.73, 30.16, 20.38; LC-MS (ESI): m/z 232[MH].

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; Ji, Qinggang; Deng, Qiao; Li, Bing; Li, Baihui; Shen, Yangli; European Journal of Medicinal Chemistry; vol. 180; (2019); p. 204 – 212;,
Bromide – Wikipedia,
bromide – Wiktionary