[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[I-].[Na+].[C:11](=O)([O-])[O-].[K+].[K+].Cl[CH2:18][CH2:19][O:20][CH3:21]>C(#N)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:11][CH2:18][CH2:19][O:20][CH3:21])=[CH:4][CH:3]=1
A mixture of 4-bromophenol (16-2, 1.01 g, 5.72 mmol), sodium iodide (1.02 g, 6.83 mmol), and potassium carbonate (1.88 g, 13.6 mmol) in acetonitrile (10.0 mL) was added with 1-chloro-2-methoxyethane (21-1, 0.89 g, 8.0 mmol). The mixture was heated to 60° C. for 48 h. The reaction mixture was cooled to room temperature and added with water (200 mL). The solution was extracted with EtOAc, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (EtOAc:hexanes=1:20 as eluant) to give 1-bromo-4-isopropoxybenzene (21-2, 0.95 g) as a colorless oil in 68% yield: 1H NMR (CDCl3) δ 7.36 (dt, J=5.0, 2.0 Hz, 2 H), 6.78 (m, 2 H), 4.02 (t, J=6.3 Hz, 2 H), 3.54 (t, J=6.1 Hz, 2 H), 3.35 (s, 3 H), 2.03 (t, J=6.2 Hz, 2 H).
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