Phenetole → HCID 71117223, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-chloro-4-methoxybenzoic acid (4, 15 g, 56.5 mmol) in toluene (72 mL) was added thionyl chloride (8.24 mL, 113 mmol) and N,N-dimethylformamide (0.1 mL). The solution was refluxed at 90° C. for 4 h, cooled to room temperature and evaporated to remove toluene and residual reagent. The obtained acyl chloride was diluted with dichloromethane (240 mL) and added portionwise aluminum chloride (8.3 g, 62.2 mmol) and phenetole (7.2 mL, 56.5 mmol) at 0° C. The reaction mixture was stirred at room temperature overnight, quenched with 1N HCl (15 mL) and H2O (15 mL). The organic layer was extracted with dichloromethane two times, washed with 1N HCl and brine, dried over magnesium sulfate, filtered and concentrated in vacuo to yield the title compound as a yellowish solid which was used without further purification.

Provenance & Evidence