Reference of 1647-23-0, A common heterocyclic compound, 1647-23-0, name is 1-Bromo-3,3-dimethylbutane, molecular formula is C6H13Br, 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.
Step 1 : A solution of A/fA/-diisopropylethytamine (2.4 mL, 17.1 mmol, 1 eq) in THF (10 mL) was cooled to -78C. A solution of /7-butyllithium in hexanes (2.5M, 6.85 mL, 17.1 eq) was added dropwise with stirring. The solution was warmed to 0C for 10 min, then cooled again to -78C. At -78C, a solution of methyl 4-(cyanomethyl)benzoate (3g, 20 mmol, 1 eq) in THF (8 mL) was added dropwise to the LDA solution (a dark red slurry formed). After stirring the resulting slurry for 10 minutes at -78C, 1-bromo-3,3- dimethylbutane (2.46 mL, 17.9 mmol, 1.05 eq) was added rapidly. The reaction was stirred for 30 minutes at -78C then was warmed to room temperature. After 1h, hexamethylphosphoramide (2.5 mL, 14 mmol) was added, and the reaction was stirred at room temperature for 16h. The reaction mixture was partitioned between EtOAc and 1N HCi. The aqueous layer was discarded, and the organic layer was washed with 1 HCI and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated to afford a crude residue which waschromatographed on silica gel (gradient elution, 0% to 30% EtOAc in hexanes, SiO2) to afford the desired product as a white crystalline solid (2.49g, 54%),
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; 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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