These common heterocyclic compound, 18599-22-9, name is 4-Bromo-3,3,4,4-tetrafluorobut-1-ene, 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. Quality Control of 4-Bromo-3,3,4,4-tetrafluorobut-1-ene
To a solution of 4-bromo-3,3,4,4-tetrafluoro-1-butene (4) (0.812g, 3.92mmol, 1.0 eq.) and 2,3-O-isopropylidene-d-glyceraldehyde (5) (2.16g, 9.40, 2.4 eq.) in THF (15.7mL) was added 1.06M MeLi/LiBr-free diethyl ether solution (8.86mL, 9.40mmol, 2.4 eq.) dropwise at -78C. The resulting mixture was stirred at the same temperature for 2h, and then quenched with saturated NH4Cl aq. The reaction mixture was extracted with Et2O three times. The combined extracts were dried over anhydrous Na2SO4, and the solvents were removed under reduced pressure. The residue was dissolved in EtOH. To this mixture was added an excess amount of NaBH4 at 0C. The resulting mixture was stirred at room temperature for several hours, and then quenched with sat. NH4Cl aq. The reaction mixture was extracted with EtOAc three times. The combined extracts were dried over anhydrous Na2SO4, and the solvents were removed under reduced pressure. The residue was chromatographed on a silica gel to give the corresponding alcohols, 6a (0.352g, 1.37mmol, 35% isolated yield, anti isomer) and 6b (0.402g, 1.58mmol, 40% isolated yield, syn isomer) as a colorless oil.
The synthetic route of 4-Bromo-3,3,4,4-tetrafluorobut-1-ene has been constantly updated, and we look forward to future research findings.
Reference:
Article; Konno, Tsutomu; Hoshino, Tomoko; Kida, Takumi; Takano, Shinya; Ishihara, Takashi; Journal of Fluorine Chemistry; vol. 152; (2013); p. 106 – 113;,
Bromide – Wikipedia,
bromide – Wiktionary