Water → 4-Fluoro-4'-methylbenzophenone

Participants

Reaction Steps

Aluminum chloride (3.74 g, 28 mmol) was added into a stirred solution of toluene 18 (60 mL) and 4-fluorobenzoyl chloride (3.42 g, 21.6 mmol). The solution was stirred at room temperature for 90 minutes, and then 5 mL of water was added dropwise to quench the reaction. The reaction mixture washed with water and 10% NaHCO3. The solution was then dried with anhydrous MgSO4. The solvent was removed from the solution to obtain a yellow solid. The yellow crude product was dissolved in a small amount of methylene chloride and hexane was added dropwise until precipitation occurred. The solution was then heated and the product was allowed to recrystallize to form 2.70 g of product (62% yield). 1H-NMR: δ 7.80 (dd, aromatic, 2H), 7.67 (d, aromatic, 2H), 7.26 (d, aromatic, 2H), 7.15 (t, aromatic, 2H), 2.42 (s, methyl, 3H). 13C-NMR: δ 195.0 (carbonyl); 166.2, 164.2, 143.3, 134.7, 132.2, 130.1, 129.0, 115.3 (aromatic); 21.6 (alkyl). 19F-NMR: δ −109.1 ppm.

Provenance & Evidence