4-Methoxybiphenyl → HCID 10928704, compound

Participants

Reaction Steps

A solution of Example 11E (282 mg, 0.946 mmol) in benzene (5 mL) was treated with thionyl chloride (0.138 mL, 1.89 mmol) and DMF (1 drop), stirred at room temperature for 30 minutes, concentrated to dryness and redissolved in dichloromethane (5 mL). The resulting solution was treated with 4-methoxybiphenyl (348 mg, 1.89 mmol) and aluminum chloride (377 mg, 2.84 mmol) at 0° C., stirred at room temperature for 40 minutes, quenched with ice-water, extracted with dichloromethane, dried (Na2SO4), filtered, concentrated and purified on silica gel with a gradient of 5% to 20% ethyl acetate/hexanes to provide 200 mg (45%) of the desired compound contaminated with 30% of the ortho substituted isomer.

Provenance & Evidence