Electric Literature of 6621-59-6,Some common heterocyclic compound, 6621-59-6, name is 6-Bromohexanenitrile, molecular formula is C6H10BrN, 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.
In a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of BnOH (3.22 g, 29.78 mmol, 1.00 equiv) in N,N- dimethylformamide (80 mL). This was followed by the addition of sodium hydride (2.05 g, 59.79 mmol, 2.00 equiv) in several batches at 0 C. The resulting solution was stirred for 30 minutes at 0 C in a water/ice bath. To this was added 6-bromohexanenitrile (5.2 g, 29.54 mmol, 1.00 equiv) in portions at 0 C. The resulting solution was allowed to react, with stirring, for an additional 3 hours at room temperature. The reaction was then quenched by the addition of 500 mL of water. The resulting solution was extracted with ethyl acetate (3×500 mL) and the combined organic layers were concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (60: 1). This resulted in 1.06 g (18%) of 6-(benzyloxy)hexanenitrile as yellow oil.
The synthetic route of 6621-59-6 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; INNATE TUMOR IMMUNITY, INC.; O’MALLEY, Daniel; GAVAI, Ashvinikumar V.; GILL, Patrice; TARBY, Christine M.; WATTERSON, Scott Hunter; GONG, Hua; WILLIAMS, David K.; GHOSH, Shomir; ROUSH, William R.; (307 pag.)WO2019/14402; (2019); A1;,
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