Tributyltin Chloride → (S)-Tributyl(2,4-difluoro-6-(pent-4-en-2-yloxy)phenyl)stannane

Participants

Reaction Steps

A solution of (S)-2-bromo-1,5-difluoro-3-(pent-4-en-2-yloxy)benzene (0.28 g, 1.01 mmol, 1 equiv) in THF (5 mL) was cooled to −78° C. (IPA/dry ice). nBuLi (0.76 mL of a 1.6 M solution in hexane, 1.21 mmol, 1.2 equiv) was added slowly. Orange color observed. After 30 min, tributyltin chloride (0.33 mL, 1.21 mmol, 1.2 equiv) was added. The reaction was stirred 30 min. The reaction was remove from the cold bath, diluted with ether, and washed with saturated aqueous NaHCO3. The ether layer was dried (MgSO4) and concentrated in vacuo to provide the crude stannane (0.60 g, 100%) as a yellow oil. Contaminated with tin byproducts, used as is. 1H NMR (400 MHz, CDCl3) δ 6.44-6.25 (m, 2H), 5.95-5.62 (m, 1H), 5.21-5.06 (m, 2H), 4.52-4.28 (m, 1H), 2.62-2.43 (m, 1H), 2.31 (dd, J=13.9, 6.7 Hz, 1H), 1.70-0.74 (m, 27H).

Provenance & Evidence