Iodine → 1-Chloro-2-fluoro-4-iodo-5-methoxybenzene
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH3:10])[CH:5]=[CH:6][C:7]=1[F:8].[I:11]I>C(Cl)(Cl)Cl.FC(F)(F)C([O-])=O.[Ag+]>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([I:11])=[C:4]([O:9][CH3:10])[CH:3]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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.
Workup
- filtrationfiltered through Celite
- washThe filtrate was washed with water, brine
- customdried
- concentrationconcentrated
- customThe crude product was purified by crystallization from ether/petroleum ether
Sources & evidence
- ORD record
- ord-ad8c45574e094de9a2cfdf9f28f0c622
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07423051B2
Reaction notes
Loading…