Tetrahydrofuran → HCID 86663206, compound

Participants

Reaction Steps

A solution of 1-bromo-2,3,5,6-tetrafluorobenzene (4.71 g, 20.57 mmol) in anhydrous THF (100 mL) was stirred in a −78° C. in dry ice/acetone bath under argon gas. After 30 min, 2.5 M n-BuLi in hexane (9.05 mmol, 22.63 mmol) was added dropwise at that temperature for 20 min. After adding, the mixture was stirred at −78° C. in the dry ice/acetone bath for 30 min, and stirred more for 10 min without the bath. And then, the solution was cooled again in the dry ice/acetone to −78° C. and a solution of R-(+)-propylene (1.44 mL, 20.57 mmol) in 10 mL anhydrous THF was added dropwise at the temperature for 10 min and stirred at ambient temperature for overnight. And then, the solution was quenched slowly by sat. NH4Cl, and stirred more for 2 h. Water (20 mL) was added and extracted with EtOAc, dried over anhydrous MgSO4, evaporated and purified by column chromatography (DCM/hexane 9/1) to give pale yellow oil (yield 49%˜59%). 1H NMR (CDCl3, 500 MHz) δ 6.97 (m, 1H), 4.12 (m, 1H), 2.89 (m, 2H), 1.45 (bs, 1H), 1.29 (d, J=6.5 Hz, 3H).

Provenance & Evidence