Iodine → 1-Chloro-2-fluoro-4-iodo-5-methoxybenzene

HRID 1371812Notes

Reaction equation

HRID 1371812 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]=1

Participants

5

Reactant 2

HCID 807IodineHCID 27735853-Chloro-4-fluoroanisole

Product 1

HCID 210706301-Chloro-2-fluoro-4-iodo-5-methoxybenzeneYield 59.8%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6212ChloroformSolvent

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

  1. filtrationfiltered through Celite
  2. washThe filtrate was washed with water, brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was purified by crystallization from ether/petroleum ether

Sources & evidence

ORD record
ord-d3cee51fb4a94744bef660dde30cdaac
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

Loading…