Iodine → 2-Iodo-3-(4-methoxyphenoxy)benzo[b]thiophene

HRID 1386985

Reaktionsgleichung

Reaktionsgleichung von HRID 1386985
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[S:11][CH:12]=2)=[CH:5][CH:4]=1.[Li]CCCC.[I:24]I>C1COCC1>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[S:11][C:12]=2[I:24])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 807IodineHCID 108249753-(4-Methoxyphenoxy)benzo[b]thiopheneHCID 178418339Butyllithium

Produkt 1

HCID 106912792-Iodo-3-(4-methoxyphenoxy)benzo[b]thiophene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 133 mg (0.52 mmol) of 3-(4-methoxyphenoxy)benzo[b]thiophene (Part A) in 3 mL of THF was treated with 0.33 mL of 1.6 M n-BuLi in hexanes (0.54 mmol) at −78° C. for 15 min and then treated with 138 mg (0.54 mmol) of I2 in 3 mL of THF. The reaction was allowed to gradually warm to room temperature and then partitioned between brine and EtOAc/hexanes. The two phases were separated, the organic phase was washed with H2O, dried over Na2SO4, and concentrated in vacuo. The residue was crystallized from hexanes to afford 143 mg (0.37 mmol; 72%) of the title compound as a solid.

Aufarbeitung

  1. custompartitioned between brine and EtOAc/hexanes
  2. customThe two phases were separated
  3. washthe organic phase was washed with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from hexanes

Quellen und Nachweise

ORD-Eintrag
ord-e24f8b5bbe76440ea6c3491bd4deaad9
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265575B1

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