Iodine → 2,3-Dihydro-7-iodo-2-methyl-5-trifluoromethoxybenzofuran

HRID 1017271Notes

Reaction equation

HRID 1017271 reaction equation
[I:1]I.[CH3:3][CH:4]1[CH2:8][C:7]2[CH:9]=[C:10]([O:13][C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:12][C:6]=2[O:5]1>C(Cl)(Cl)Cl.FC(F)(F)C([O-])=O.[Ag+]>[I:1][C:12]1[C:6]2[O:5][CH:4]([CH3:3])[CH2:8][C:7]=2[CH:9]=[C:10]([O:13][C:14]([F:15])([F:17])[F:16])[CH:11]=1

Participants

5

Reactant 2

HCID 807IodineHCID 184034092,3-Dihydro-2-methyl-5-trifluoromethoxybenzofuran

Product 1

HCID 184034062,3-Dihydro-7-iodo-2-methyl-5-trifluoromethoxybenzofuranYield 99.3%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6212ChloroformSolvent

Procedure

Iodine (2.8 g, 11 mmol) was added in few portions to a stirred mixture of 2,3-dihydro-2-methyl-5-trifluoromethoxybenzofuran (Description 21; 2.8 g, 12.8 mmol), silver(I) trifluoroacetate (3.5 g, 15.8 mmol) in chloroform (60 ml). The mixture was stirred at room temperature for 1 hour, filtered through a pad of Celite™ and concentrated. The residue was treated with iso-hexane (150 ml), washed with aqueous sodium sulphite. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:diethyl ether 0-4%) to give the title compound (3.76 g, 85%).

Workup

  1. filtrationfiltered through a pad of Celite™
  2. concentrationconcentrated
  3. additionThe residue was treated with iso-hexane (150 ml)
  4. washwashed with aqueous sodium sulphite
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (iso-hexane:diethyl ether 0-4%)

Sources & evidence

ORD record
ord-dc4d2c35bd584d4ea6ce4fa7ae821b67
Source dataset
uspto-grants-2002_11
Patent number
US06479486B2

Reaction notes

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