Reaction #312574

Reaction equation

Anisole

4-fluorobenzoyl chloride

HCl

Aluminum chloride

→

4-fluoro-4′-methoxy-benzophenone

Yield 94.4%

Solvents

dichloromethane

water

Conditions

Workup

1. 1
   workup.ADDITIONpoured it
2. 2
   Otherseparated
3. 3
   Extractionthe aqueous layer was extracted with 2 portions of dichloromethane (300 mL each)
4. 4
   Washwashed with saturated aqueous sodium bicarbonate (400 mL)
5. 5
   DryingThe organic layer was dried over anhydrous sodium sulfate
6. 6
   Otherevaporated

Procedure

Anisole (27.5 grams), 4-fluorobenzoyl chloride (35 grams) and dichloromethane (250 mL) were combined in a reaction flask. Aluminum chloride (30.8 grams) was added to the reaction mixture slowly over 20 minutes. Stirred the reaction mixture at room temperature for two hours and then poured it into a mixture of 70 mL concentrated HCl and 500 mL of water. The layers were phase separated and the aqueous layer was extracted with 2 portions of dichloromethane (300 mL each). The organic portions were combined and washed with saturated aqueous sodium bicarbonate (400 mL). The organic layer was dried over anhydrous sodium sulfate and evaporated to yielding 48.0 grams of 4-fluoro-4′-methoxy-benzophenone as a white solid. This material was not purified further but was used directly in the next step.

Source