4-Methoxy-alpha-toluenethiol → 2,5-Dichloro-1-methoxy-3-((4-methoxybenzyl)sulfanyl)benzene

Participants

Reaction Steps

To a mixture of DIPEA (5.77 mL), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.488 g), 1-bromo-2,5-dichloro-3-methoxybenzene (4.32 g) and (4-methoxyphenyl)methanethiol (2.47 mL) and toluene (100 mL) was added tris(dibenzylideneacetone)dipalladium (0) (Pd2(dba)3, 0.773 g) at room temperature. The mixture was refluxed for 5 h. After cooling, water was added to the mixture and the mixture was extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (5.66 g).

Provenance & Evidence