[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([C:8]2[C:9]([OH:15])=[CH:10][CH:11]=[CH:12][C:13]=2[Cl:14])[CH:7]=1.[CH3:17][C@@H:18](O)[CH2:19][CH:20]=[CH2:21].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([C:8]2[C:9]([O:15][C@H:20]([CH2:19][CH:18]=[CH2:17])[CH3:21])=[CH:10][CH:11]=[CH:12][C:13]=2[Cl:14])[CH:7]=15′-Bromo-6-chloro-2′-methyl-[1,1′-biphenyl]-2-ol (540 mg, 1.82 mmol, 1.0 equiv) were mixed with (R)-pent-4-en-2-ol (313 mg, 3.63 mmol, 2.0 equiv) and Ph3P (952 mg, 3.63 mmol, 2.0 equiv) in THF (6 ml). To this solution was added DEAD (1653 μl, 3.63 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/hex to afford 5-bromo-2′-chloro-2-methyl-6′-((S)-pent-4-en-2-yloxy)-1,1′-biphenyl (350 mg, 52.7%). 1H NMR (400 MHz, CDCl3) δ 7.39 (dd, J=8.2, 2.1 Hz, 1H), 7.25-7.21 (m, 2H), 7.14 (d, J=7.5 Hz, 1H), 7.07 (d, J=8.0 Hz, 1H), 6.86 (dd, J=8.0, 5.3 Hz, 1H), 5.66-5.50 (m, 1H), 5.05-4.90 (m, 2H), 4.35-4.24 (m, 1H), 2.30-2.12 (m, 2H), 2.01 (s, 3H), 1.16 (dd, J=11.0, 6.0 Hz, 3H). LCMS (M+1)=365.0.
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