Iodine chloride → HCID 59838025, compound

HRID 1438133Notes

Reaction equation

HRID 1438133 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[O:12][CH3:13])(=[O:3])[CH3:2].[I:14]Cl>C(Cl)Cl>[C:1]([O:4][C:5]1[CH:10]=[C:9]([I:14])[C:8]([F:11])=[CH:7][C:6]=1[O:12][CH3:13])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 59838040HCID 59838040, compound

Product 1

HCID 59838025HCID 59838025, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 64A (850 mg, 4.6 mmol) in CH2Cl2 (5.0 mL) was added ICl (1.0 M in CH2Cl2, 10.2 mL, 10.2 mmol). The mixture was stirred at 50° C. for 4 h and then at rt for 18 h. The reaction was quenched by a sat. solution of NaHCO3. After extraction with CH2Cl2, the organic layer was washed with a solution of Na2S2O3, brine and dried over Na2SO4. After evaporation of the solvent, the crude product was purified by column chromatography (EtOAc:hexanes=1:4) to give 64B (1.22 g, 80% yield) as a solid. 1H NMR (400 MHz, CDCl3) δ ppm 2.29 (s, 3H) 3.81 (s, 3H) 6.73 (d, J=9.23 Hz, 1H) 7.35 (d, J=6.59 Hz, 1H).

Workup

  1. waitat rt for 18 h
  2. customThe reaction was quenched by a sat. solution of NaHCO3
  3. extractionAfter extraction with CH2Cl2
  4. washthe organic layer was washed with a solution of Na2S2O3, brine
  5. dry with materialdried over Na2SO4
  6. customAfter evaporation of the solvent
  7. customthe crude product was purified by column chromatography (EtOAc:hexanes=1:4)

Sources & evidence

ORD record
ord-5c92930ee2fd47b69a2e12ba6195a789
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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