2-Chloroethyl methyl sulfide → 2-Methoxy-4-(2-methylsulfanyl-ethoxy)-1-nitro-benzene

Participants

Reaction Conditions

Reaction Steps

Step A To a solution of 3-methoxy-4-nitrophenol (0.5 g, 3 mmol) prepared in Example 132 Step A in anhydrous DMF (13 mL) were added K2CO3 (0.8 g, 5.9 mmol) and 1-Chloro-2-methylsulfanyl-ethane (Aldrich)(0.65 g, 5.9 mmol) sequentially. The reaction mixture was heated at 70° C. for 2 h. The mixture was cooled to room temperature, and diluted with water. The mixture was extracted with ethyl acetate three times. The combined organic extract was washed with water, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (0-40% EtOAc in hexanes) to give 2-methoxy-4-(2-methylsulfanyl-ethoxy)-1-nitro-benzene as a white solid (0.25 g, 35%).

Provenance & Evidence