Month: November 2020

1435-51-4, 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.

1,3-dibromo-5-fluorobenzene (10.0 g, 39.0 mmol) in tetrahydrofuran (10 mL) was added dropwise to a stirred solution of isopropylmagnesium chloride (1.3M in tetrahydrofuran, 36.0 mL, 46.0 mmol) in tetrahydrofuran (100 mL) at 0 C, and the reaction mixture was then stirred at room temperature for 3 hours. The reaction mixture was cooled to 0 C and N,N-dimethylformamide (9.63 mL, 11.7 mmol) was added dropwise to the reaction mixture and stirred at room temperature for 1 hour. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water followed by brine, dried (Na2SO4), filtered, concentrated to afford the title compound as light brown gum (6.0 gm, 75%). The crude material was used for next reaction without purification.

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; Cortendo AB; Blass, B. E.; Abou-Gharbia, M. A.; Childers, W. E.; Iyer, P.; Boruwa, J.; (143 pag.)CN105722823; (2016); A;,
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

52997-43-0, Adding some certain compound to certain chemical reactions, such as: 52997-43-0, name is 7-(Bromomethyl)pentadecane, 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 52997-43-0.

General procedure: General procedure for the synthesis of a1-a6: To a solution of indoline-2,3-diones (10 mmol) in DMF (40 mL) was added K2CO3(15 mmol, 2.073 g) and 7-(bromomethyl)pentadecane (11 mmol,3.358 g) under nitrogen. The mixture was stirred at 70 C and monitoredby TLC. After the reaction completed, water was added, andextracted with EtOAc. The organic layer was combined and dried withMgSO4. After evaporation of the solvent, the residue was purified bycolumn chromatograph (eluent: Petroleum/EtOAc=20:1) to give thetarget compound. 1-(2-Hexyldecyl)indoline-2,3-dione (a1) Orange oil, 3.46 g, 93%.FT-IR (KBr) nu=1743 and 1612 cm-1 (C]O). 1H NMR (400 MHz,CDCl3) delta 7.60-7.55 (m, 2H), 7.10 (dd, J1=7.2 Hz, J2=7.6 Hz, 1H),6.86 (d, J=8.0 Hz, 1H), 3.59 (d, J=7.2 Hz, 2H), 1.86-1.81 (m, 1H),1.34-1.23 (m, 24H), 0.88-0.83 (m, 6H); 13C NMR (100 MHz, CDCl3) delta183.28, 158.19, 151.21, 138.20, 124.90, 123.32, 117.29, 110.30,44.42, 35.78, 31.64, 31.54, 31.27, 29.73, 29.40, 29.29, 29.06, 26.12,26.09, 22.44, 22.41, 13.88, 13.84. ESI-MS(100%, negative) m/z=371.2 (M-).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 52997-43-0.

Reference:
Article; Hu, Qian; Jiang, Hua; Cui, Zhihua; Chen, Weiguo; Dyes and Pigments; vol. 173; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

1435-53-6, A common compound: 1435-53-6, name is 2,4-Dibromo-1-fluorobenzene, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 195N-(4-(3-methyl-lH-1,2,4-triazol-1-yl)phenyl)-4-(2-(methylsulfonyl)-5- morpholinophenyl)pyrimidin-2-aminePart I: 4-(3-bromo-4-(methylsulfonyl)phenyl)morpholine[0353] A mixture of 2,4-dibromo-1-fluorobenzene (1.0 g, 4.0 mmol), NaSMe (0.33 g, 4.8 mmol), triethylamine (0.52 rnL, 4.0 mmol) and dimethylacetamide (3 mL) in a sealed tube was heated up to 100C for 12 hr. The reaction mixture was cooled, diluted with EtOAc and washed with brine. The organic layer was separated, dried (MgSO4) and concentrated to give a crude residue which was purified by chromatography on silica gel (EtOAc/hexanes) to afford (2,4-dibromophenyl)(methyl)sulfane.[0354] 4-(3-bromo-4-(methylsulfonyl)phenyl)morpholine was obtained by following procedure O utilizing morpholine and 2,4-dibromo-1-(methylsulfonyl)benzene which was prepared from (2,4-dibromophenyl) (methyl) sulfane following the protocol as described forExample 43.

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-Dibromo-1-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; WO2009/32861; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan, 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 955959-84-9, 955959-84-9

6.3 g (15.4 mmol) of N-phenyl-3,3-bicarbazole, 5.0 g (15.4 mmol) of 4-(4-bromophenyl)dibenzo[b,d]furan, 3.0 g (30.7 mmol) of sodium t-butoxide, 0.9 g (1.5 mmol) of tris(dibenzylideneacetone)dipalladium, and 1.2 mL of tri t-butylphosphine (50% in toluene) were mixed with 100 mL of xylene in a 250 mL round flask, and the mixture was heated and refluxed under a nitrogen flow for 15 hours. The obtained mixture was added to 300 mL of methanol, and a solid crystallized therein was filtered, dissolved in dichlorobenzene, filtered with silica gel/Celite, and after removing an appropriate amount of an organic solvent, recrystallized with methanol to obtain Compound B-78 (7.3 g, a yield of 73%). (0183) calcd. C48H30N2O: C, 88.59; H, 4.65; N, 4.30; O, 2.46. found: C, 88.56; H, 4.62; N, 4.20; 0, 2.43.

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-(4-Bromophenyl)dibenzo[b,d]furan, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SAMSUNG SDI CO., LTD.; JUNG, Ho Kuk; LUI, Jinhyun; KIM, Dong-Yeong; JANG, Kipo; HUH, Dal-Ho; YU, Eun Sun; JUNG, Sung-Hyun; (75 pag.)US2019/280211; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

51437-00-4, Adding a certain compound to certain chemical reactions, such as: 51437-00-4, name is 4-Bromo-1-fluoro-2-methylbenzene, 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 51437-00-4.

To an oven dried three neck flask was added Mg turnings (355 mg, 14.6 mg-at.) catalytic amount of iodine, and 20 mL THF. To the resulting mixture was added dropwise 4-bromo-1-fluoro-2-methyl-benzene (1.0 g, 0.005 mol) with heating to 62 C. After completing the addition of the aryl bromide, the mixture was stirred for an additional 30 min at 62 C. The THF solution of the prepared aryl magnesium bromide was cooled to -70 C. and succinic anhydride (1.0 g, 0.01 mmol) added as a solution in 10 mL THF. The mixture was vigorously stirred with warming to rt over 3 h and then hydrolyzed by the addition of 30 mL of 1M HCl. The resulting mixture was extracted with ethyl acetate (2¡Á20 mL). The combined organic layers were extracted with 5% aqueous K2CO3 (3¡Á10 mL) and the combined aqueous layers acidified with 1M HCl to pH3. A milky colloidal suspension was extracted with ethyl acetate (3¡Á30 mL) and the combined organic layers washed with brine (2¡Á20 mL). The solvent was evaporated under reduced pressure and the crude product used directly in the next step without further purification.LC/MS: tR=6.0 min. MS (API-ES) m/z 211 (M+H+).

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-1-fluoro-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PanThera Biopharma, LLC; US2010/286125; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

A common compound: 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 67567-26-4

To a solution of 4-bromo-2,6-difluoroaniline (10 g, 48 mmol) in DCM (15mL) was added ethyl 3-chloro-3-oxopropanoate (6.8 mL, 53 mmol) and DIEA (9.2 mL,53 mmol) and the reaction mixture stirred for 1 h. The reaction mixture was partitioned between H20 and DCM and the layers separated. The DCM portion was washed with satd. NH4C1 and H20 then dried (Na2SO4) and filtered. The filtrate was concentrated under reduced pressure to give Compound 90a(10 g, 65% yield). LCMS = 1.60 mmusing analytical method (Q), 321.9 (M+H). 1HNMR(500MHz, CDC13) oe 8.89 (br. s.,1H), 7.20 – 7.15 (m, 2H), 4.29 (q, J=7.2 Hz, 2H), 3.54 (s, 2H), 1.36 – 1.31 (m, 3H).

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; BRISTOL-MYERS SQUIBB COMPANY; JOHNSON, James A.; JIANG, Ji; KIM, Soong-Hoon; PI, Zulan; QIAO, Jennifer X.; TORA, George O.; WANG, Tammy C.; FINLAY, Heather; WO2014/11513; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

22385-77-9, The chemical industry reduces the impact on the environment during synthesis 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, I believe this compound will play a more active role in future production and life.

Preparation 13 ,5-Di-/er/-butylbenzaldehydeDissolve l-bromo-3,5-di-/er/-butylbenzene (5.00 g, 18.57 mmol) in THF (50 mL) under a nitrogen atmosphere. Cool to -78 C. Slowly add w-butyllithium (2.5 M in hexanes) (22.29 mL, 55.72 mmol) at -78 C. Stir at -78 C for about 30 min. Add DMF (4.31 mL, 55.72 mmol) dropwise. Warm the mixture to 0 C and stir for 2.5 h. Pour aqueous NH4CI (30 mL) into the mixture. Extract with EtOAc (3 x 20 mL). Dry the combined organic portions over a2S04; filter; collect the filtrate; and concentrate under reduced pressure. Purify the residue using flash chromatography eluting with a gradient of 0-10% EtO Ac/petroleum ether to afford the title compound (2.96 g, 73%) as a white solid. LC-ES/MS m/z 219 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3,5-di-tert-butylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ELI LILLY AND COMPANY; BLEISCH, Thomas, John; COATES, David, Andrew; HUGHES, Norman, Earle; JONES, Scott, Alan; NORMAN, Bryan, Hurst; WO2013/66640; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

A common heterocyclic compound, 73918-56-6, name is 2-(4-Bromophenyl)ethanamine, molecular formula is C8H10BrN, 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. 73918-56-6.

2-(4-Bromophenyl)-ethylamine (13, 10.0g, 50mmol) and NaOH (3.0g, 75mmol) were dissolved in the mixture of dioxane (150mL) and H2O (150mL). The reaction mixture was cooled to 0C. The solution of di-tert-butyl dicarbonate (16.36g, 75mmol) in dioxane (72mL) was added dropwise to the reaction mixture, which was stirred at room temperature for 5.5h. Dioxane was removed in vacuo and the residue was extracted with ethyl acetate 3 times. The combined organic layer was washed with water and brine, and then dried over anhydrous Na2SO4. Filtration and removal of solvent provided the crude product, which was purified by Combiflash chromatography (5-10% of ethyl acetate in hexane). The title compound 5 (13.5g, 90.0%) was obtained as a white solid; mp 59-60C. 1H NMR (300MHz, chloroform-d): delta=7.42 (d, J=8.0Hz, 2H), 7.07 (d, J=8.0Hz, 2H), 4.51 (br. s, 1H), 3.40-3.27 (m, 2H), 2.75 (t, J=6.9Hz, 2H), 1.43 (s, 9H). MS (EI): m/z=300.1 (M++H).

The synthetic route of 2-(4-Bromophenyl)ethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qiao, Chang-Jiang; Ali, Hamed I.; Ahn, Kwang H.; Kolluru, Srikanth; Kendall, Debra A.; Lu, Dai; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 517 – 529;,
Bromide – Wikipedia,
bromide – Wiktionary

583-70-0, 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 583-70-0 as follows.

Example 1; Isopropyl 2-(2,4-dimethylphenyl)benzenesulfonate (Compound 11); [0056] A solution of isopropyl 2-(4,4,5,5-tetramethyl-l,3-dioxolan-2- yl)benzenesulfonate (0.65 g, 2.0 mmol, 1.0 equiv) and l-bromo-2,4-dimethylbenzene (0.37 g, 2.1 mmol, 1.05 equiv) in toluene (15 mL) was degassed, and Pd(OAc)2 was added followed by tri(o-tolyl)phosphine, and 3 mL of a degassed 2N aqueous K2CO3 solution. The mixture was stirred at 800C for 20 hours and then water (10 mL) was added and extracted with EtOAc. The organic layer was washed with brine and dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (20:1 hexanes/EtOAc) to afford Compound 11. 1H NMR (500 MHz, CDCIa) 8.13 (dd, J = 8.1, 1.2 Hz, IH), 7.61 (ddd, J = 7.6, 7.6, 1.4 Hz, IH), 7.50 (ddd, J = 8.1, 7.6, 1.4 Hz, IH), 7.26 (dd, J = 7.5, 1.2 Hz, IH), 7.08-7.01 (m, 3H), 4.73- 4.65 (m, IH), 2.36 (s, 3H), 2.03 (s, 3H), 1.26 (d, J= 6.3 Hz, 3H), 1.15 (d, J= 6.3 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 583-70-0, and friends who are interested can also refer to it.

Reference:
Patent; PHARMACOPEIA, LLC; ZHI, Lin; PICKENS, Jason; VAN OEVEREN, Cornelius, A.; HENDERSON, Ian; WO2010/135350; (2010); A2;,
Bromide – Wikipedia,
bromide – Wiktionary