Methyl iodide → 4-Bromo-3-fluorothioanisole

A solution of 4-bromo-3-fluoro-benzenethiol (225 mg, 1.09 mmol) in tetrahydrofuran (3 ml) was cooled to 0° C. Sodium hydride (60% dispersion in mineral oil, 52 mg, 1.31 mmol) was added and the mixture was stirred for 5 minutes. Iodomethane (78 μl, 1.25 mmol) was then added and the mixture was allowed to return to room temperature with stirring over 20 minutes. Dichloromethane (10 ml) was added and the reaction was quenched with 1 M aqueous hydrochloric acid. The layers were separated and the organic layer was washed with water, dried (MgSO4), then concentrated in vacuo. The residue was purified by flash chromatography (Si-PPC, pentane:diethyl ether, gradient 100:0 to 90:10) to afford the title compound as a bright yellow oil (208 mg, 86%). 1H NMR (CDCl3, 400 MHz) 7.43 (1H, dd, J=8.4, 7.2), 7.00 (1H, dd, J=9.4, 2.3), 6.91 (1H, ddd, J=8.4, 2.1, 0.7), 2.48 (3H, s).

1. customto return to room temperature
2. stirringwith stirring over 20 minutes
3. customthe reaction was quenched with 1 M aqueous hydrochloric acid
4. customThe layers were separated
5. washthe organic layer was washed with water
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo
8. customThe residue was purified by flash chromatography (Si-PPC, pentane:diethyl ether, gradient 100:0 to 90:10)

ORD record

ord-2a373ceec0224672b67c3da9308e80b1

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07855216B2