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

HRID 1693732Notes

Reaction equation

HRID 1693732 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[F:10].[I:11]I>C(Cl)(Cl)Cl.FC(F)(F)C([O-])=O.[Ag+]>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([I:11])=[CH:4][C:3]=1[F:10]

Participants

5

Reactant 2

HCID 807IodineHCID 27735853-Chloro-4-fluoroanisole

Product 1

HCID 210706301-Chloro-2-fluoro-4-iodo-5-methoxybenzeneYield 81.3%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6212ChloroformSolvent

Procedure

Silver trifluoroacetate (23.2 g, 105.0 mmol) was added to a solution of 2-chloro-1-fluoro-4-methoxy-benzene (5 g, 29.2 mmols) in chloroform (250 ml), followed by iodine (15.8 g, 62.2 mmol) in several portions. The mixture was stirred at room temperature for 2 hours and filtered through Celite. The filtrate was washed with water, brine, dried with Na2SO4, decanted, and concentrated to dryness. Silica chromatography of the crude using a gradient of ethyl acetate and hexane afforded 1-chloro-2-fluoro-4-iodo-5-methoxy-benzene (6.8 g, 81% yield). 1H NMR (500 MHz, DMSO-d6) δ 3.83 (s, 3H), 7.22 (d, 1H), 7.88 (d, 1H).

Workup

  1. filtrationfiltered through Celite
  2. washThe filtrate was washed with water, brine
  3. dry with materialdried with Na2SO4
  4. customdecanted
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1e637634f6b74e8da5d59f5cf7b2204e
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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