Sodium Iodide → 1,1'-Biphenyl, 3-iodo-

HRID 1424770Notes

Reaction equation

HRID 1424770 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[I-:14].[Na+].CNC1CCCCC1NC>[Cu]I.O1CCOCC1>[I:14][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 164493-BromobiphenylHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamine

Product 1

HCID 885421,1'-Biphenyl, 3-iodo-Yield 92%

Reagents, catalysts & solvents 2

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

Procedure

3-bromo-1,1′-biphenyl (5.00 g, 21.5 mmol), sodium iodide (6.43 g, 42.9 mmol), copper(I) iodide (1.226 g, 6.43 mmol), and dioxane (214 ml) were added into a 500 mL 3-necked flask. N1,N2-dimethylcyclohexane-1,2-diamine (1.691 ml, 10.72 mmol) was then added. The solution was heated and refluxed overnight. Upon completion of the reaction, the reaction mixture was cooled to room temperature, filtered through a pad of celite and washed several times with dichloromethane. The solvents are evaporated under vacuum and the crude material was purified via column chromatography using hexane/DCM (90/10). The target 3-iodo-1,1′-biphenyl (5.5 g, 19.64 mmol, 92% yield) was afforded as a colorless oil.

Workup

  1. temperatureThe solution was heated
  2. temperaturerefluxed overnight
  3. customUpon completion of the reaction
  4. filtrationfiltered through a pad of celite
  5. washwashed several times with dichloromethane
  6. customThe solvents are evaporated under vacuum
  7. customthe crude material was purified via column chromatography

Sources & evidence

ORD record
ord-c0ddb56dc32646379d212a3fd927a23e
Source dataset
uspto-grants-2015_01
Patent number
US08927749B2

Reaction notes

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