Triphenylphosphine → 5-bromo-2,2'-difluoro-6'-((S)-pent-4-en-2-yloxy)-1,1'-biphenyl

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Reaction Steps

5′-Bromo-2′,6-difluoro-[1,1′-biphenyl]-2-ol (520 mg, 1.82 mmol., 1.0 equiv) were mixed with (R)-pent-4-en-2-ol (314 mg, 3.65 mmol, 2.0 equiv) and Ph3P (957 mg, 3.65 mmol, 2.0 equiv) in THF (6 mL). To this solution was added DEAD (1661 μl, 3.65 mmol, 2.0 equiv) dropwise and stirred overnight. The solution was mixed with silica gel and concentrated and purified by 40 g ISCO column with 0-10% EtOAc/hexane to afford 5-bromo-2,2′-difluoro-6′-((S)-pent-4-en-2-yloxy)-1,1′-biphenyl (500 mg, 78%). 1H NMR (400 MHz, CDCl3) δ 7.52-7.42 (m, 2H), 7.34-7.28 (m, 1H), 7.03 (t, J=9.0 Hz, 1H), 6.81-6.74 (m, 2H), 5.81-5.62 (m, 1H), 5.12-4.96 (m, 2H), 4.41 (dq, J=11.7, 5.9 Hz, 1H), 2.44-2.18 (m, 2H), 1.23 (dd, J=7.3, 6.3 Hz, 3H). LCMS (M+1)=353.1.

Provenance & Evidence