Isophthaloyl chloride → 1-(3-Methylbenzoyl),3-(3-methylbenzoyl)benzene

Participants

Reaction Conditions

Reaction Steps

3-bromotoluene (6.684 g, 39.08 mmol) was dissolved in anhydrous tetrahydrofuran (30 mL) under an inert atmosphere of nitrogen. The solution was stirred for 5 min and cooled to −78° C. followed by the dropwise addition of n-butyllithium in hexanes (2.5M; 13.6 mL). After stirring for 3.5 h, the Weinreb amide of isophthaloyl dichloride was added dropwise and the solution was stirred for 1 h at −78° C. The reaction mixture was quenched with 1 M HCl (40 mL) and the products were extracted with dichloromethane (2×50 mL). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Purification using flash chromatography (silica gel, hexanes:ethyl acetate, gradient, 95:5 to 70:30) afforded 2.465 g, 9.77 mmol) 1-(3-methylbenzoyl),3-(3-methylbenzoyl)benzene 8 in a 72% yield.

Provenance & Evidence