[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F: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>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F: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]=1
5′-Bromo-6-chloro-2′-fluoro-[1,1′-biphenyl]-2-ol (750 mg, 2.49 mmol, 1.0 equiv) were mixed with (R)-pent-4-en-2-ol (428 mg, 4.97 mmol, 2.0 equiv) and PPh3 (1305 mg, 4.97 mmol, 2.0 equiv) in tetrahydrofuran (8 mL). To this solution was added DEAD (2266 μl, 4.97 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′-chloro-2-fluoro-6′-((S)-pent-4-en-2-yloxy)-1,1′-biphenyl (385 mg, 42%). 1H NMR (400 MHz, CDCl3) δ 7.49-7.44 (m, 1H), 7.41-7.36 (m, 1H), 7.29 (s, 1H), 7.11-6.99 (m, 2H), 6.87 (dd, J=8.3, 2.0 Hz, 1H), 5.73-5.56 (m, 1H), 5.07-4.93 (m, 2H), 4.36 (dq, J=8.8, 6.0 Hz, 1H), 2.37-2.16 (m, 2H), 1.20 (dd, J=6.0, 3.0 Hz, 3H). LCMS (M+1)=369.0.
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