Sodium Iodide → HCID 90387091, compound

HRID 1424765Notes

Reaction equation

HRID 1424765 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[S:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:12]=3[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[I-:21].[Na+].CNC1CCCCC1NC>[Cu]I.O1CCOCC1>[I:21][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[S:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:12]=3[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 59866480HCID 59866480, compound

Product 1

HCID 90387091HCID 90387091, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

4-(3-bromophenyl)dibenzo[b,d]thiophene (9.00 g, 26.5 mmol), sodium iodide (7.95 g, 53.1 mmol), copper(I) iodide (1.516 g, 7.96 mmol), and dioxane (265 ml) were added into a 500 mL 3-necked flask. N1,N2-dimethylcyclohexane-1,2-diamine (2.092 ml, 13.26 mmol) was added. The mixture was degassed by bubbling nitrogen for 30 minutes and the reaction mixture was heated and refluxed overnight. After completion of the reaction, the heating was stopped and the mixture was filtered through a pad of Celite® and washed several times with DCM. The crude material was purified via column chromatography using hexane/DCM (80/20). The target 4-(3-iodophenyl)dibenzo[b,d]thiophene (9.33 g, 24.16 mmol, 91% yield) was afforded as a white solid.

Workup

  1. customThe mixture was degassed
  2. customby bubbling nitrogen for 30 minutes
  3. temperaturethe reaction mixture was heated
  4. temperaturerefluxed overnight
  5. customAfter completion of the reaction
  6. filtrationthe mixture was filtered through a pad of Celite®
  7. washwashed several times with DCM
  8. customThe crude material was purified via column chromatography

Sources & evidence

ORD record
ord-4f7ba487c26b4031bcc5d72c41a2f2b6
Source dataset
uspto-grants-2015_01
Patent number
US08927749B2

Reaction notes

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