Category: bromides-buliding-blocks

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 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

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

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

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

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

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

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

1003-98-1, 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. 1003-98-1 name is 2-Bromo-4-fluoroaniline, 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-Propyl-3-propyl-5-fluoro-1H-indole; A 50 mL three neck flask was charged with palladium acetate (22.4 mg, 0.1 mmol), dtbpf (94 mg, 0.2 mmol), potassium carbonate (690 mg, 5 mmol), 2-bromo-4-fluoroaniline (380 mg, 2 mmol), 4-octyne (264 mg, 2.4 mmol) and NMP (10 ml). The mixture was purged with argon and heated to 130 C. After 1 hr, the reaction mixture was cooled to rt. Ethyl acetate and water were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic phases were washed with water, brine and dried with MgSO4. Removal of the solvents and purification of the crude by column chromatography afforded the desired product as yellow oil (355 mg, containing 4.3 wt % AcOEt). The corrected yield was 77.6%. 1H NMR (400 MHz): delta=7.68 (s, 1H), 7.16-7.13 (m, 2H), 6.83 (td, 1H, J=9.2 Hz, J=2.4), 2.68 (t, 2H, J=7.6 Hz), 2.61 (t, 2H, J=7.6), 1.72-1.57 (m, 4H), 0.98 (t, 3H, J=7.2 Hz), 0.95 (t, 3H, J=7.2 Hz).

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; Boehringer Ingelheim International GmbH; US2005/209465; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 876-53-9, name is 1,3-Dibromoadamantane, 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 876-53-9, 876-53-9

1. Under nitrogen protection, 440 g of 1,3-dibromoadamantane was added to a 10 L four-necked flask. Then 2.0 L of dichloroethane was added and stirred well, 500 g of acetanilide was added and stirred well. Add zinc dichloride slowly and stir it well, then heat up to reflux (internal temperature 80-85C). Partially separate the water with a water separator and then use a reflux device. After refluxing at this temperature for 24 hours, the lower layer was a viscous solid and the upper layer was a dichloroethane solvent. Cool to room temperature, pour off the upper layer of solvent, add 1.0L DMF (N,N-dimethylformamide) to raise the temperature to a solid slurry, and slowly pour the slurry into 4.0L of stirring water. Stir 30%. Filter after minutes The solid crude product was obtained in a wet weight of 1219 g. The solid was added to 6 L of water for beating for 3.5 hours, filtered and pumped until no liquid was dripped, and then washed with water (2¡Á2 L). 1332 g of crude wet weight was obtained, refluxed with two-fold volume of ethanol (3 L) for 1 hour, cooled to room temperature and stirred at room temperature for 1 hour, filtered to dry wet weight 522 g and used directly for the second reaction.

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-Dibromoadamantane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Bodong Chemical Technology Co., Ltd.; Fu Zhiwei; He Baoyuan; Pan Xingang; Yu Wenqing; Li Yongli; Lu Wei; (7 pag.)CN107673977; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary