Methyl iodide → 1-Bromo-2-chloro-4-methylsulfanyl-benzene

Participants

Reaction Conditions

Reaction Steps

4-Bromo-3-chloro-benzenethiol (0.94 g, 4.21 mmol) was dissolved in tetrahydrofuran (10 ml) and cooled to 0° C. under argon. Sodium hydride (0.19 g, 4.63 mmol) was added and the mixture was stirred for 5 minutes, then iodomethane (0.28 ml, 4.42 mmol) was added. The mixture was allowed to warm, stirring for 30 minutes, then the reaction was quenched with saturated aqueous ammonium chloride. The mixture was extracted with dichloromethane (×2) and the combined organic layers were dried (MgSO4) and concentrated. Purification of the resultant residue by flash chromatography (Si-PCC, pentane) afforded the title compound as a colourless oil (0.65 g, 65%). 1H NMR (CDCl3 400 MHz) 2.47 (3H, s), 6.99 (1H, dd, J=8.45, 2.26 Hz), 7.30 (1H, d, J=2.25 Hz), 7.48 (1H, d, J=8.45 Hz).

Provenance & Evidence