Sodium Iodide → 1-Bromo-4-(3-methoxypropoxy)benzene

Temperature

60 °C

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).

1. temperatureThe reaction mixture was cooled to room temperature
2. extractionThe solution was extracted with EtOAc
3. dry with materialdried over MgSO4
4. concentrationconcentrated in vacuo
5. customThe residue was purified by flash column chromatography on silica gel (EtOAc:hexanes=1:20 as eluant)

ORD record

ord-076b0e50185948219270ee2f8e49d426

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999983B2