Ethylenediamine → 4-Iodobiphenyl

HRID 2253510Notes

Reaction equation

HRID 2253510 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Na+].[I-:15].C(N)CN.S1(CCCC1)(=O)=O>[Cu]I.CCCCCC>[I:15][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 3301EthylenediamineHCID 5238Sodium IodideHCID 71014-BromobiphenylHCID 31347Sulfolane

Product 1

HCID 153224-IodobiphenylYield 94%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8058HexaneSolvent

Conditions

Temperature
130 °C

Procedure

A Schlenk tube was charged with CuI (19.5 mg, 0.102 mmol, 10 mol %), 4-bromobiphenyl (234 mg, 1.00 mmol), NaI (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ethylenediamine (13.5 μL, 0.202 mmol, 20 mol %) and sulfolane (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 130° C. for 23 h. The resulting suspension was allowed to reach room temperature, poured into hexane (20 mL) and washed with water (3×20 mL). The combined organic phases were dried (MgSO4), concentrated, and the residue was purified by flash chromatography on silica gel (hexane) to provide 262 mg (94% yield) of 4-iodobiphenyl as white crystals.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customto reach room temperature
  4. washwashed with water (3×20 mL)
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. concentrationconcentrated
  7. customthe residue was purified by flash chromatography on silica gel (hexane)

Sources & evidence

ORD record
ord-cc95ea12c6b040b5bb18466da49a85c6
Source dataset
uspto-grants-2008_01
Patent number
US07323608B2

Reaction notes

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