Reaction #58422

Reaction equation

3-chloro-4-fluoroanisole

iodine

→

5-chloro-4-fluoro-2-iodoanisole

Yield 59.8%

Solvents

chloroform

Conditions

Workup

1. 1
   Filtrationfiltered through Celite
2. 2
   WashThe filtrate was washed with water, brine
3. 3
   Otherdried
4. 4
   Concentrationconcentrated
5. 5
   OtherThe crude product was purified by crystallization from ether/petroleum ether

Procedure

To a solution of 3-chloro-4-fluoroanisole (4.69 g, Lancaster) in chloroform (250 mL) was added silver trifluoroacetate (23.2 g, Aldrich) followed by iodine (15.8 g, Aldrich) in several portions. The reaction mixture was stirred for 2 hours and filtered through Celite. The filtrate was washed with water, brine, dried and concentrated. The crude product was purified by crystallization from ether/petroleum ether to give 5-chloro-4-fluoro-2-iodoanisole (5.0 g). MS (M+H)+, 285.

Source