Ethyl Acetate → 3,5-Dimethyl-4-(3'-iso-propyl-4'-methoxyphenylsulfanyl)anisole

Participants

Reaction Steps

Copper iodine (70 mg, 0.37 mmol), neocuprinine (80 mg, 0.37 mmol) and potassium t-butoxide (470 mg, 4.05 mmol) were added in this order to a solution of 4-methoxy-3-iso-propyl-thiophenol (U.S. Pat. No. 6,747,048 B2, 600 mg, 2.3 mmol) and 3,5-dimethyl-4-iodoanisole (678 mg, 3.72 mmol) in toluene (10 mL). After refluxing overnight, the cooled reaction mixture was poured into ethyl acetate (50 mL) and washed twice with 1 N HCl then brine. The organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, hexane/ethyl acetate 100:0 to 40:1) to give 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxyphenylsulfanyl)anisole (0.358 g, 49%); 1H NMR (200 MHz, DMSO-d6): δ 6.87-6.80 (m, 4H), 6.56 (m, 1H), 3.76 (s, 3H), 3.71 (s, 3H), 3.15 (m, 1H), 2.34 (s, 6H), 1.06 (d, 6H, J=7 Hz); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=25% ethyl acetate in hexane; Rf=0.36

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