Electric Literature of 5414-19-7,Some common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, molecular formula is C4H8Br2O, 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 of ethylsulfone acid 833a (2.06 g, 8.79 mmol) in anhydrous THF at-78C under N2 was added LiHMDS solution (19.3 mL, 1.0 Min THF). The mixture was stirred at-78C for 30 min before it was allowed to warmed to 0C along with a cold acetone bath. It was then re-cooled to-78C and to it was added 2-bromoethyl ether (1.8 mL, 13. 2 mmol). After stirred at- 78C for 30 min, the mixture was warmed to rt and stirred for 2 h. It was again re-cooled to-78C and to it was added LiHMDS solution (10.6 mL, 10.6 mmol). After stirred at-78C for 30 min, the mixture was warmed to rt and stirred for 3 h before it was quenched with 1 N aqueous HCI solution until the pH is about 1-2. The solution was extracted with CH2CI2 (2×450 mL). Combined organic solution was dried (MgS04), filtered and concentrated. The crude product was dissolved in 1 N NaOH solution (300 mL) and extracted with EtOAc (100 mL). After layers were separated, the organic solution was washed with 1 N NaOH (2×150 mL). The combined aqueous solution was acidified to pH-1 using 6 N HCI solution. It was extracted with EtOAc (3 x 300 mL). The organic solutions were combined, dried (MgSO4), filtered and concentrated to give 2.3 g product (833b; 7.56 mmol, 89%).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2-(2-bromoethoxy)ethane, its application will become more common.
Reference:
Patent; SCHERING CORPORATION; WO2005/87731; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem