Extracurricular laboratory: Synthetic route of 2695-48-9

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 of 2695-48-9, A common heterocyclic compound, 2695-48-9, name is 8-Bromo-1-octene, molecular formula is C8H15Br, 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.

A suspension of Mg (30.6 mg, 1.26 mmol) and 8-bromo-1-octene (0.20 mL, 1.19 mmol) in THF (10 mL) was stirredat 50C. After being stirred for 1 h, Mg solid was perfectlyconsumed. To a solution of 9 (0.11 mL, 1.00 mmol) and NiCl2(16.3 mg, 0.0300 mmol) in THF (5.0 mL) was added the prepared7-octenylmagnesium bromide at 0C and the mixturewas stirred at room temperature for 1 h. After the additionof sat. NH4Cl aq. (30 mL) at 0C, the reaction mixture wasextracted with EtOAc (10 mL × 3), dried over MgSO4, andconcentrated under reduced pressure. The residue was purifiedby silica gel column chromatography (hexane-EtOAc = 5 : 1)to afford 7 (67.6 mg, 0.290 mmol, 29%) as a colorless oil.

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:
Article; Kutsumura, Noriki; Inagaki, Mai; Kiriseko, Akito; Saito, Takao; Chemical and Pharmaceutical Bulletin; vol. 67; 6; (2019); p. 594 – 598;,
Bromide – Wikipedia,
bromide – Wiktionary