Iodine → HCID 67057738, compound

HRID 604604Notes

Reaction equation

HRID 604604 reaction equation
[I:1]I.[C:3]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[F:15])([CH3:6])([CH3:5])[CH3:4]>CCO.S([O-])([O-])(=O)=O.[Ag+2]>[C:3]([C:7]1[CH:12]=[C:11]([I:1])[C:10]([O:13][CH3:14])=[CH:9][C:8]=1[F:15])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 807IodineHCID 23560869HCID 23560869, compound

Product 1

HCID 67057738HCID 67057738, compound

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

Iodine (1.24 g, 4.90 mmol) and silver sulfate (1.53 g, 4.90 mmol) were added successively to a stirred solution of 1-tert-butyl-2-fluoro-4-methoxybenzene and 3-fluororanisole (0.755 g, 4.90 mmol) in EtOH (38.3 mL) at room temperature under N2. The mixture was stirred at room temperature for 4 h, then filtered through a plug of Celite. The mixture was partitioned between 50% saturated Na2SO3 and Et2O. The aqueous layer was separated and extracted with Et2O (×2). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to remove volatile byproducts and afford 1-tert-butyl-2-fluoro-5-iodo-4-methoxybenzene. Rf=0.34 (100% hexanes). 1H NMR (600 MHz, CDCl3): δ 7.63 (d, J=9.0 Hz, 1H); 6.53 (d, J=13.8 Hz, 1H); 3.84 (s, 3H); 1.33 (s, 9H).

Workup

  1. filtrationfiltered through a plug of Celite
  2. customThe mixture was partitioned between 50% saturated Na2SO3 and Et2O
  3. customThe aqueous layer was separated
  4. extractionextracted with Et2O (×2)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto remove volatile byproducts

Sources & evidence

ORD record
ord-535a4fa1b27140adae5ab3141a1781bb
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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