Category: 14659-58-6

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. 14659-58-6, name is 2-Bromo-5-fluoro-1,3-dimethylbenzene, This compound has unique chemical properties. The synthetic route is as follows., category: bromides-buliding-blocks

A solution of 2-bromo-5-fluoro-1,3-dimethylbenzene (25 g, 123 mmol) in tetrahydrofuran (300 mL) was cooled to -78 C and n-butyllithium (59.1 mL, 148 mmol) wasadded dropwise at a rate to keep the internal temperature at or below -75 C. The mixture was stirred for 2 hours and then trimethylborate (16.51 mL, 148 mmol) was added and the mixture stirred for 3 hours at -78 C, then warmed to ambient temperature. After 4 hours, the mixture was cooled to -10 C and a precooled solution of NaOH (7.39 g, 185 mmol) and 30 % hydrogen peroxide (201 mL, 1970 mmol) was added. Once the addition was completethe mixture was allowed to warm to ambient temperature overnight. The pH of the mixture was adjusted to pH 1 with 2M HC1. 400 mL of ethyl ether and 200 mL of water were added and the layers were separated. The aqueous layer was extracted with 3 x 200 mL of ether, and the combined organic layers were washed with saturated NaHCO3 and saturated Na5203, then stirred with a saturated aqueous Na5205 solution (200 mL) for 15 minutes. The organicphase was dried with anhydrous magnesium sulfate, filtered, and concentrated. The residues were taken up in 1/1 diethyl ether/pentane and flushed through a silica plug. Concentration of the filtrate provided 11 .47g (67%) of the title compound.

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 14659-58-6.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; FIDANZE, Steven D.; HASVOLD, Lisa A.; LIU, Dachun; MCDANIEL, Keith F.; PRATT, John; SCHRIMPF, Michael; SHEPPARD, George S.; WANG, Le; LI, Bing; (191 pag.)WO2017/177955; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 14659-58-6, 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. 14659-58-6 name is 2-Bromo-5-fluoro-1,3-dimethylbenzene, 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.

In Step 2, Compound 78 (10 g) was converted Compound 79 using methyl 2- mercaptoacetate in piperidine/pyridine at 100 C. The reaction was stirred for 4 hour prior to purification that yielded Compound 79 (11.7 g). In Step 3, Compound 79 (2 g) was converted to benzothiophene Compound 72 using SOCI2 in xylenes/pyridine. The reaction was heated to 120 C and allowed to stir overnight. In Step 4, Compound 72 is subjected to n-butyl lithium and 2- bromo-5-fluoro-1,3-dimethylbenzene to afford Compound 73. In Step 5, Compound 73 is demethylated using BBr3 to afford Compound 74. In Step 6, Compound 74 is reacted with sodium hydride and benzyl bromide to afford Compound 75. In Step 7, Compound 75 is mixed with Compound 38 and cesium carbonate in DMSO to afford Compound 76. In Step 8, the benzyl protecting group of Compound 76 is removed by hydrogenation to afford Compound 112.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-fluoro-1,3-dimethylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; G1 THERAPEUTICS, INC.; STRUM, Jay, Copeland; (187 pag.)WO2020/37251; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

14659-58-6, name is 2-Bromo-5-fluoro-1,3-dimethylbenzene, 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. name: 2-Bromo-5-fluoro-1,3-dimethylbenzene

A 1L three-necked round-bottomed flask equipped with a magnetic stir bar was charged with di-tert-butyl (2′, 4′, 6′-triisopropyl- [1, 1′-biphenyl] -2-yl) phosphine (8.37 g, 19.70 mmol) , tris (dibenzylideneacetone) dipalladium (4.51 g, 4.92 mmol) and potassium hydroxide (41.4 g, 739 mmol) . The flask was evacuated and backfilled with nitrogen. Separately, dioxane (150 mL) , 2-bromo-5-fluoro-1, 3-dimethylbenzene (50 g, 246 mmol) and water (150 mL) were flow purged with nitrogen for about 30 minutes and were transferred to the reaction flask via a cannula. The reaction vessel was heated to about 100 C and stirred overnight. The reaction mixture was cooled to ambient temperature. The reaction mixture was acidified to pH 2 by adding 6N HCl and the product was extracted with dichloromethane (3 x 250 mL) . The combined organic layers were stirred with mercaptopropyl silica gel for about 30 minutes, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford the title compound as a white solid. (31.2 g, 223 mmol, 90% yield)

The synthetic route of 14659-58-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; COWART, Marlon; FIDANZE, Steven; HASVOLD, Lisa; LIU, Dachun; MCDANIEL, Keith; PRATT, John; SHEPPARD, George; WANG, Le; (241 pag.)WO2018/68283; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary