Methyl iodide → 1-Bromo-4-(2-methoxyethyl)benzene

To a solution of 2-(4-bromophenyl)ethanol (1 g, 5 mmol) in anhydrous THF (10 mL) was added NaH (60% oil dispersion, 0.2 g, 5 mmol). The mixture was stirred at room temperature for 30 min and cooled to −0° C. Iodomethane (920 mg, 6.5 mmole) was added slowly to the mixture and stirred for 8 h. The reaction mixture was then quenched by adding water, extracted with ethyl acetate. The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 5% ethyl acetate in hexane) to give the title compound as a colorless (1 g, 93% yield). 1H NMR (CDCl3, 400 MHz): 7.39 (d, 2H), 7.08 (d, 2H), 3.56 (t, 2H), 3.33 (s, 3H), 2.82 (t, 2H); MS (ESI) m/z. Calc. 215.1 (M+). Found: 216.3 (M′+1), 218.1 (M++3).

1. temperaturecooled to −0° C
2. stirringstirred for 8 h
3. customThe reaction mixture was then quenched
4. additionby adding water
5. extractionextracted with ethyl acetate
6. dry with materialThe combined organic extracts were dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by flash chromatography (silica gel, 5% ethyl acetate in hexane)

ORD record

ord-66ff9a3ce82b4013a954fa62f4960a40

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08334292B1