Application of 1647-23-0,Some common heterocyclic compound, 1647-23-0, name is 1-Bromo-3,3-dimethylbutane, molecular formula is C6H13Br, 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.
Ste S; The grignard reagent was made as follows: Magnesium turnings (2.4 g, 100 mmol) were suspended in dry Et2O (150 ml) under N2. A few iodine crystals were added to the mixture. The 1 -bromo-3,3-diemthyl butane (16.5 g, 100 mmol) in Et20 (50 ml) was added in portions over ~ 45 minutes to maintain gentle reflux. After the addition of all of the 1-bromo-3,3-diemthyl butane, the reaction was refluxed for 2 nr. The gringnard solution was used as is in the next step.The grignard reagent (100 mmol in 200 ml of Et20) was added to a solution of the imine (9.9 g, 33.5 mmol) at -78C. The solution was siowly warmed to RT. After stirring at RT for 2 h, the reaction was quenched with sat. NH4CI(aq.) at 0 C. Ethyl acetate was added, and the mixture was stirred at RT for 1 h. The layers were separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine and dried (MgS04). The mixture was filtered and concentrated. The residue was purified via gradient flash chromatography (0-40% EtOAc in hexanes, SiO2). The major fraction was recrystallized from heptane/IPA which yielded 2.8 g of the desired product. The mother liquor was recrystallized once again to provide an additional 1.3 g (32 % total).
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-3,3-dimethylbutane, its application will become more common.
Reference:
Patent; SCHERING CORPORATION; WONG, Michael, K.; LAVEY, Brian, J.; YU, Wensheng; KOZLOWSKI, Josheph, A.; DEMONG, Duane, E.; DAI, Xing; STAMFORD, Andrew, W.; MILLER, Michael, W.; ZHOU, Guowei; YANG, De-Yi; GREENLEE, William, J.; WO2011/119559; (2011); A1;,
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