Iodine → 2-Bromo-3-[4-(2-ethylhexyl)-phenyl]-5-iodothiophene

HRID 1175090Notes

Reaction equation

HRID 1175090 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([CH2:19][CH3:20])[CH2:15][CH2:16][CH2:17][CH3:18])=[CH:9][CH:8]=1.II.C(O)(=O)C.C(O)(=O)C.[I:31]C1C=CC=CC=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>>[Br:1][C:2]1[S:3][C:4]([I:31])=[CH:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([CH2:19][CH3:20])[CH2:15][CH2:16][CH2:17][CH3:18])=[CH:9][CH:8]=1

Participants

5

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 12217721Iodo benzene diacetateHCID 595582522-Bromo-3-[4-(2-ethylhexyl)-phenyl]-thiophene

Product 1

HCID 595582582-Bromo-3-[4-(2-ethylhexyl)-phenyl]-5-iodothiophene

Procedure

The procedure was adapted from Yokoyama, A. Macromolecules 2004, 37, 1169. A 100-mL round bottom flask was charged with 2-bromo-3-[4-(2-ethylhexyl)-phenyl]-thiophene (2.6 g, 7.4 mmol), purged with N2, and anhydrous dichloromethane (18 mL) was added via a deoxygenated syringe. The reaction flask was cooled down to 0° C., whereupon iodine (I2) (1.04 g, 4.1 mmol) and iodobenzene diacetate (PhI(OAc)2) (1.4 g, 4.4 mmol) were added in one portion, and the mixture was stirred at ambient temperature for 4 hours. An aqueous solution of sodium thiosulfate (NaS2O3) (10%) was added to the reaction mixture; the aqueous layer was separated and extracted with diethyl ether (3×50 mL). The collected organic phase was washed with aqueous NaS2O3 (10%) and dried over anhydrous MgSO4. After filtration, the solvent and iodobenzene were removed by evaporation under reduced pressure. The crude product was purified using column chromatography on silica gel with hexane as the eluent (Rf=0.38). The compound was dried under vacuum to yield 3.35 g (95%) of slightly yellow oil.

Workup

  1. custompurged with N2, and anhydrous dichloromethane (18 mL)
  2. additionwas added via a deoxygenated syringe
  3. additionwere added in one portion
  4. customthe aqueous layer was separated
  5. extractionextracted with diethyl ether (3×50 mL)
  6. washThe collected organic phase was washed with aqueous NaS2O3 (10%)
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationAfter filtration
  9. customthe solvent and iodobenzene were removed by evaporation under reduced pressure
  10. customThe crude product was purified
  11. customThe compound was dried under vacuum
  12. customto yield 3.35 g (95%) of slightly yellow oil

Sources & evidence

ORD record
ord-34e26a47bb4e4fcda6941db09a5e5801
Source dataset
uspto-grants-2010_11
Patent number
US07838624B2

Reaction notes

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