[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:18])=[C:6]([CH:17]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=1.[CH2:19](Br)[CH:20]=[CH2:21].[OH-].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:21]([O:16][CH2:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][C:6]2[CH:17]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[Cl:18])=[CH:9][CH:10]=1)[CH:20]=[CH2:19]
A mixture of 2-(4-(5-bromo-2-chlorobenzyl)phenyl)ethanol (intermediate BH) (245 mg, 0.75 mmol), allyl bromide (2.6 mL, 3.01 mmol), potassium hydroxide (84 mg, 1.5 mmol) and tetra-n-butylammonium iodide (13.9 mg, 0.037 mmol) was stirred at room temperature for 6 h. Water (1 mL) was added and extracted with chloroform (3×1 mL), washed with brine (1 mL) and dried (Na2SO4), filtered and evaporated. Preparative TLC using 10:1 hexane:EtOAc gave intermediate BI (246 mg, yield 89%). 1H NMR (300 MHz, CDCl3): δ 7.26-7.08 (m, 7H), 5.90 (m, 1H), 5.22 (m, 2H), 4.02 (s, 2H), 3.99 (m, 2H), 3.64 (t, J=6.9, 7.2 Hz, 2H), 2.89 (t, J=6.9, 7.2 Hz, 2H).
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