(4-hydroxyphenyl)-(2-methylphenyl)methanone

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under argon, 4-hydroxyphenyl 2-methylphenyl ketone (1.334 g) obtained in Example 126 and 4-dimethylaminopyridine (845 mg) were added to xylene (15 ml), and the admixture was stirred at room temperature for 1 hour. 4-Chloro-6,7-dimethoxyquinoline (1.406 g) was added, and the admixture was refluxed with heat for 23 hours. The reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform, and the chloroform layer was then dried with anhydrous magnesium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate and then with chloroform, followed by thin layer chromatography on silica gel eluting with hexane/acetone (2/1), to obtain 1.258 g of the title compound (yield: 50%). the admixture was refluxed with heat for 23 hours The reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform the chloroform layer was then dried with anhydrous magnesium sulfate After removing the solvent by reduced-pressure distillation the resulting residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Methoxyphenyl 2-methylphenyl ketone (1.660 g) obtained in Example 125 was dissolved in chloroform (10 ml), a solution of 1.0 M boron tribromide in dichloromethane (29 ml) was added while cooled in ice, and the admixture was stirred at room temperature overnight. A solution of 1.0 M boron tribromide in dichloromethane (15 ml) was further added, and the admixture was stirred at room temperature for 2 days. The reaction mixture was then treated in the same manner as described in Example 121 to obtain 1.501 g of the title compound (yield: 96%). while cooled in ice the admixture was stirred at room temperature for 2 days The reaction mixture was then treated in the same manner