Acetonitrile → 3-((4-Methoxybenzyl)sulfanyl)-2,5-dimethylphenyl acetate

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-hydroxy-2,5-dimethylphenyl acetate (1.04 g) and CH3CN (57 mL) were added TEA (1.61 mL) and Tf2O (1.17 mL) at 0° C. The mixture was stirred at 0° C. for 30 min under nitrogen atmosphere. The mixture was diluted with water at 0° C. and then concentrated in vacuo. The residue was extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residual crude material was dissolved in toluene (50 mL). To the solution were added DIPEA (1.79 mL), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.150 g), (4-methoxyphenyl)methanethiol (0.723 mL) and tris(dibenzylideneacetone)dipalladium (0) (Pd2(dba)3, 0.238 g) at room temperature. The mixture was refluxed for 4 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 (1.27 g).

Provenance & Evidence