Month: September 2021

Electric Literature of 1435-53-6, A common heterocyclic compound, 1435-53-6, name is 2,4-Dibromo-1-fluorobenzene, molecular formula is C6H3Br2F, 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: 8.1 1,3-Diphenyl-4-fluorobenzene (11a): Starting with 10 (100 mg, 0.39 mmol), Cs2CO3 (253 mg, 0.78 mmol), Pd(PPh3)4 (3 mol%), phenylboronic acid (94 mg, 0.78 mmol) and 1,4-dioxane (4 mL), 11a was isolated as a colorless oil (54 mg, 55%). 1H NMR (300 MHz, CDCl3): delta = 7.09-7.16 (m, 1H, ArH), 7.23-7.32 (m, 2H, ArH), 7.33-7.45 (m, 5H, ArH), 7.47-7.63 (m, 5H, ArH). 13C NMR (75 MHz, CDCl3): delta = 116.3 (d, J = 23.6 Hz, CH), 127.1 (2CH), 127.6 (d, J = 8.02 Hz, CH), 128.6 (2CH), 128.9 (2CH), 129.1 (CH), 129.6 (CH), 130.9 (CH), 132.5 (C), 135.8 (C), 137.7 (d, J = 3.57 Hz, C), 140.2 (C), 159.4, (d, JCF = 249.0 Hz, CF). 19F NMR (282 MHz, CDCl3): delta = -120.67 (CF). IR (ATR, cm-1): , 3029 (w), 2956 (w), 2927 (w), 2857 (w), 1948 (w), 1883 (w), 1806 (w), 1723 (m), 1600 (w), 1539 (w), 1478 (s), 1392 (w), 1332 (w), 1257 (m), 1183 (w), 1121 (m), 1073 (m), 1000 (w), 945 (w), 892 (m), 823 (s), 759 (s), 721 (m), 693 (s), 631 (s), 584 (s), 539 (m). MS (EI, 70 eV); m/z (%) = 248 (100) [M]+. HRMS (EI) calcd. for C18H13OF [M]+: 248.09958; found 248.89357.

The synthetic route of 1435-53-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sharif, Muhammad; Maalik, Aneela; Reimann, Sebastian; Feist, Holger; Iqbal, Jamshed; Patonay, Tamas; Villinger, Alexander; Langer, Peter; Journal of Fluorine Chemistry; vol. 146; (2013); p. 19 – 36;,
Bromide – Wikipedia,
bromide – Wiktionary

320-29-6, name is 4-Bromo-1,2-bis(trifluoromethyl)benzene, 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. HPLC of Formula: C8H3BrF6

Sodium Hydride (60% oil suspension, 5 mmol, 200 mg) is triturated with hexane and suspended in N,N-dimethylformamide (4 mL). 1,2,3,9-Tetrahydro-carbazol-4-one (2.5 mmol, 462 mg) is added to the water-cooled suspension. After 5 minutes, 5-bromo-2-trifluorobenzotrifluoride (5 mmol, 0.71 g) is added. The reaction is stirred at 85 degrees Celsius for 3.5 h. The reaction mixture is allowed to cool and is extracted into ethyl acetate (200 mL) and is washed with water (50 mL). The organic phase is dried over magnesium sulfate. Filtration, followed by concentration, and silica gel chromatography affords the desired 9-(4-Bromo-2-trifluoromethyl-phenyl)-1,2,3,9-tetrahydro-carbazol-4-one as a brown foam (0.74 g, 73%).

The synthetic route of 320-29-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Serenex, Inc.; US2007/185184; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 6627-78-7, 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. 6627-78-7 name is 1-Bromo-4-methylnaphthalene, 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.

2.21 g (10 mmol) of compound V-2And 3.76 g (20 mmol) of B(i-PrO)3 dissolved in 14 mL of dry toluene and 7 mL of THF.Stir and cool to -30 C under nitrogen.Then, 6.25 mL (10 mmol) of a 1.6 M n-BuLi n-hexane solution was slowly added dropwise with a syringe.After the dropwise addition was completed, the reaction mixture was stirred at this temperature for 3 hours.Then stir at room temperature for another 3 hours.TLC tracking revealed that the reaction was complete.1 mL of concentrated hydrochloric acid was slowly added to the reaction mixture, and the mixture was stirred at room temperature for 1 hour.Then, it was poured into 200 mL of ice water, stirred, extracted with 50 mL of ×3CH2Cl2, and the combined phases were combined, washed with 100 mL of 5% brine, and dried over anhydrous sodium sulfate.The desiccant was removed by suction filtration, and the filtrate was evaporated to dryness on a rotary evaporator.Compound VI-2 was obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-methylnaphthalene, and friends who are interested can also refer to it.

Reference:
Patent; Foshan Sai Weisi Pharmaceutical Technology Co., Ltd.; Cai Ziyang; (9 pag.)CN108129453; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1003-99-2, name is 2-Bromo-5-fluoroaniline, 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 1003-99-2, HPLC of Formula: C6H5BrFN

General procedure: Method I. Compounds 1a-1e and 3b were synthesized using a modified procedure.1 Substituted aniline (1.0 equiv.) was added to a round-bottom flask. The flask was fitted with a rubber septum and purged with nitrogen gas, and acetic anhydride (1M in CH2Cl2, 1.1 equiv.) was added at room temperature. The reaction was refluxed overnight and monitored by TLC. Upon completion the reaction mixture was quenched with H2O. The resulting mixture was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anh. Na2SO4, filtered, then concentrated in vacuo to give the product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Article; Lasing, Thitiya; Phumee, Atchara; Siriyasatien, Padet; Chitchak, Kantima; Vanalabhpatana, Parichatr; Mak, Kit-Kay; Hee Ng, Chew; Vilaivan, Tirayut; Khotavivattana, Tanatorn; Bioorganic and Medicinal Chemistry; vol. 28; 1; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

39478-78-9,Some common heterocyclic compound, 39478-78-9, name is 5-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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 solution 5-bromo-2-methyl aniline (6.38 g, 36.74 mmol) in EtOH (30 ml) was added acetonyl acetone (5.0 ml, 42.62 mmol) and one drop of conc. aqueous HCl. The mixture was heated at reflux for 18 h and then cooled. Solvent was evaporated to dryness under reduced pressure and the residue was partitioned between water and EtOAc. The organic layer was separated and washed with water and brine dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the residue by flash chromatography (hex:EtOAc/8:2) gave 5.8 g of 1-(5-bromo-2-methyl-phenyl)-2,5-dimethyl-1H-pyrrole (60%) as a clear oil.

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-2-methylaniline, its application will become more common.

Reference:
Patent; Brotherton-Pleiss, Christine E.; Caroon, Joan Marie; Lopez-Tapia, Francisco Javier; Walker, Keith Adrian Murray; US2011/28502; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 348-57-2, name is 1-Bromo-2,4-difluorobenzene, 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. name: 1-Bromo-2,4-difluorobenzene

EXAMPLE 19 Preparation of 4-(2,4-difluorophenyl)-anisole from 4-methoxyphenylmagnesiumbromide and palladium chloride/triphenylphosphine (0.05percent) A suspension of magnesium turnings (1.54 g; 63.3 mmoles-Pometon) in tetrahydrofuran (16.02 g) was heated at 65° C. under stirring and under nitrogen. Then, iodine (0.02 g) and, after 30 minutes, 4-bromoanisole (11.69 g; 62.5 mmoles), in 1 hour, were added to the reaction mixture. At the end of the addition, the reaction mixture was kept at 75° C. for 1 hour and, then, decanted obtaining a solution of 4-methoxyphenylmagnesiumbromide (solution A). A mixture of 1-bromo-2,4-difluorobenzene (11.4 g; 59.1 mmoles), palladium chloride (0.00526 g; 0.0297 mmoles–Fluka) and triphenylphosphine (0.03088 g; 0.1177 mmoles–Fluka) was de-aerated by vacuum/nitrogen at 25° C. The mixture was heated at 85° C., kept under stirring for 15 minutes and, then, solution A was added in 3 hours. At the end of the addition, the reaction mixture was kept at 85° C. for 30 minutes. After cooling at 60° C., a solution of 37percent hydrochloric acid (2 ml) in water (10 ml) was added in 20 minutes. The mixture was cooled at 40° C. and the phases were separated. The solvent of the organic phase was evaporated under reduced pressure obtaining the desired compound (98.5percent yield).

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

Reference:
Patent; Zambon Group S.p.A.; US5312975; (1994); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 129316-09-2, The chemical industry reduces the impact on the environment during synthesis 129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene, I believe this compound will play a more active role in future production and life.

Step 1 : 1-(3-Bromo-5-(te t-butyl)phenyl)ethanone (P49a) To a solution of 1 ,3-dibromo-5-(fert-butyl)benzene (664 mg, 2.22 mmol) in toluene (15 mL) were added tri-n-butyl-1-ethoxyvinyl tin (965 mg, 2.66 mmol) and Pd(PPh3)2CI2 (150 mg 0.22 mmol) under N2. The mixture was stirred at 95C for 3 h, evaporated, diluted with 1 ,4-dioxane and 2N HCI, stirred rapidly at 25C for 1h and then extracted with EA. The combined organic layers were washed with brine, dried over Na2S04, concentrated and purified by CC to afford compound P49a (310 mg, 55%).

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, 1,3-Dibromo-5-(tert-butyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas; WO2012/139775; (2012); A1;,
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. 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, A new synthetic method of this compound is introduced below., Product Details of 1435-51-4

Ice bath, the 2M Isopropylmagnesium chloride (10 mL, 20 mmol) was dissolved in 5 mL of tetrahydrofuran, A solution of 1,3-dibromo-5-fluorobenzene 40a (4.0 g, 15.70 mmol) In tetrahydrofuran,Stirred for 2 hours, and then heated to 20 C reaction for 30 minutes. Cool down to 0 C,N, N-Dimethylformamide (2.5 mL, 31.50 mmol) was added dropwise,The reaction was stirred for 1.5 hours,The reaction was stirred at room temperature for 12 hours.The reaction was quenched by the addition of 20 mL of saturated ammonium chloride solution, extracted with ethyl acetate (50 mL of X3) and the organic phases were combined, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure and eluted with silica gel column chromatography eluent system B The resulting residue was purified to give the title product 3-bromo-5-fluorobenzaldehyde 40b (2.57 g, yellow liquid), yield: 81.0%.

The synthetic route of 1435-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHANGHAI HENGRUI PHARM CO LTD; JIANGSU HENGRUI MEDICINE CO LTD; Lyu, HEJUN; DONG, QING; FEI, HONGBO; JIANG, HONGJIAN; SONG, PENG; (114 pag.)CN103030646; (2016); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 35354-37-1, name is 1-Bromo-5-methylhexane, 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 35354-37-1, name: 1-Bromo-5-methylhexane

(a) Methyl 1-(5-methylhexyl)cyclopentanecarboxylate To a solution of methyl cyclopentanecarboxylate (300 mg, 2.3 mmol) in THF (20 ml) at -78° C. was added LHMDS (4.6 mL, 4.6 mmol) and stirred for 30 min, and followed by 1-bromo-5-methylhexane (626 mg, 3.5 mmol). The mixture was stirred from -78° C. to rt over 16 hr, before 30 ml of H2O was added and then was extracted with CH2Cl2 (2*30 mL). The combined extracts were washed with water, dried over MgSO4, filtered and concentrated, then purified using flash chromatography to give an oil (110 mg, 21percent). MS [M+H]+333.

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; Yang, Michael G.; Liu, Hong; US2002/61874; (2002); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 19190-91-1, name is 5,6-Dibromo-1,2-dihydroacenaphthylene, molecular formula is C12H8Br2, 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. Recommanded Product: 19190-91-1

General procedure: Dibromoarene 1 (0.5 mmol), alkyne 2 (0.6 mmol), Pd(OAc)2 (5 mol%, 5.6 mg ),Xantphos (5.5 mol%,16 mg), K2CO3 (1.5 mmol, 207 mg) were added into a Schlenkflask. The flask was evacuated and backfilled with nitrogen (3 cycles). Dry DMF (5mL) was added by syringe. The mixture was heated to 120 C and stirred until thereaction finished (TLC analysis). After cooling to room temperature, the mixture wasextracted three times with ethyl acetate. The organic layers were combined and driedover Na2SO4. After filtration, the solvents were evaporated. The crude product wasfurther purified by silica gel chromatography, using petroleum ether and ethyl acetateas eluents to provide the pure product

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19190-91-1, its application will become more common.

Reference:
Article; An, Wenbo; Li, Gaoqiang; Ma, Jun; Tian, Youping; Xu, Feng; Synlett; vol. 25; 11; (2014); p. 1585 – 1590;,
Bromide – Wikipedia,
bromide – Wiktionary