Iodine → HCID 11112679, compound

HRID 1976351Notes

Reaction equation

HRID 1976351 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:21])[CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[O:10]2)=[C:5]([OH:22])[CH:4]=1.C([O-])(=O)C.[Tl+].[I:28]I.[Tl]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:21])[CH:8]=[C:9]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)[O:10]2)=[C:5]([OH:22])[C:4]=1[I:28]

Participants

6

Reactant 4

HCID 807IodineHCID 11247thallium(I) acetateHCID 5281601Apigenin dimethyletherHCID 5359464Thallium

Product 1

HCID 11112679HCID 11112679, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6 (2.98 g, 10.0 mmol) in 300 mL CH2Cl2 was added thallium(I) acetate (3.16 g, 10.2 mmol). With magnetic stirring, a solution of iodine (2.54 g, 10.0 mmol) in 200 mL CH2Cl2 was added dropwise over 1 h. During the addition, a fine suspension of thallium salts precipitated. The solution was stirred at room temperature overnight, then filtered through a bed of celite to remove the precipitated salts. The filtrate was extracted sequentially with 500 mL each of 5% NaHCO3, 10% Na2S2O4, and saturated brine, then dried over magnesium sulfate and filtered. Evaporation in vacuo provided an orange solid. Recrystallization from 300 mL CHCl3/EtOH (1:2) afforded fine yellow needles (3.10 g, 73.1%); mp 227-228° C. (lit.13 mp 205-207° C.); 1H NMR (CDCl3) δ 3.90 (s, 3 H), 4.00 (s, 3 H), 6.54 (s, 1 H), 6.64 (s, 1 H), 7.02 (d, 2 H, J=9.0 Hz), 7.85 (d, 2 H, J=9.0 Hz), 13.84 (s, 1 H); 13C NMR (75 MHz, CDCl3) δ 181.7, 164.4, 163.5, 162.9, 161.3, 158.3, 128.2, 123.3, 114.6, 104.4, 104.3, 90.5, 90.4, 56.8, 55.5; EI-MS m/z 424 (M+, 100). Anal. calcd for C17H13IO5: C, 48.14; H, 3.09. Found: C, 48.30; H, 3.11.

Workup

  1. additionDuring the addition
  2. customprecipitated
  3. filtrationfiltered through a bed of celite
  4. customto remove the precipitated salts
  5. extractionThe filtrate was extracted sequentially with 500 mL each of 5% NaHCO3, 10% Na2S2O4, and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customEvaporation in vacuo
  9. customprovided an orange solid
  10. customRecrystallization from 300 mL CHCl3/EtOH (1:2)

Sources & evidence

ORD record
ord-659b4e3f7fa941ed8fcb7c1db0b5e916
Source dataset
uspto-grants-2001_05
Patent number
US06225481B1

Reaction notes

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