1,3-Propanediamine → 4-Iodobiphenyl

HRID 2253543Notes

Reaction equation

HRID 2253543 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)CCN.C(O)CCCC>N.[Cu]I.O>[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

8

Reactant 4

HCID 4281,3-PropanediamineHCID 5238Sodium IodideHCID 62761-PentanolHCID 71014-Bromobiphenyl

Product 1

HCID 153224-IodobiphenylYield 96%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 222AmmoniaSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), 4-bromobiphenyl (234 mg, 1.00 mmol), NaI (300 mg, 2.00 mmol), evacuated and backfilled with argon. 1,3-Propanediamine (8.4 μL, 0.10 mmol, 10 mol %) and n-pentanol (1.0 m -L) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 130° C. for 22 h. The resulting suspension was allowed to reach room temperature, diluted with 30% aq ammonia (2 mL), poured into water (20 mL), and extracted with dichloromethane (3×15 mL). The combined organic phases were dried (MgSO4), concentrated, and the residue was purified by flash chromatography on silica gel (hexane) to provide 269 mg (96% yield) of 4-iodobiphenyl as a white solid. Mp: 113-114° C. (lit. 112.5-113.5° C. See lbuki, E.; Ozasa, S.; Murai, K. Bull. Chem. Soc. Jpn. 1975, 48, 1868). The 1H and 13C spectra matched those reported in Dektar, J. L.; Hacker, N. P. J. Org. Chem. 1990, 55, 639.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customto reach room temperature
  4. extractionextracted with dichloromethane (3×15 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-d3d1c97fb0f74b6cadc42efa8cbd50f1
Source dataset
uspto-grants-2008_01
Patent number
US07323608B2

Reaction notes

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