Imidazole → 1,4-Dichloro-2-(5-iodopent-1-ynyl)benzene

HRID 395383Notes

Reaction equation

HRID 395383 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]#[C:10][CH2:11][CH2:12][CH2:13]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:39]I>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]#[C:10][CH2:11][CH2:12][CH2:13][I:39]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 223207595-(2,5-Dichlorophenyl)pent-4-yn-1-ol

Product 1

HCID 129889421,4-Dichloro-2-(5-iodopent-1-ynyl)benzeneYield 72.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-(2,5-Dichlorophenyl)pent-4-yn-1-ol (13.7 g, 59.8 mmol), triphenylphosphine (20.4 g, 77.8 mmol), and imidazole (5.71 g, 83.8 mmol) in a mixed solvent (100 ml acetonitrile-150 ml ether) was stirred under nitrogen at 0° C., and to this was slowly added iodine (21.3 g, 83.8 mmol). The solution was allowed to warm to room temperature and stirring was continued for 18 hours. This was chromatographed on silica gel with hexane to give the title compound (14.7 g, 72%), MS m/z 337.9 (M−H calcd. for C11H9Cl2I=338.0).

Workup

  1. customThis was chromatographed on silica gel with hexane

Sources & evidence

ORD record
ord-6749d3ecd3f24a1ebce3e3d2ad31d8e4
Source dataset
uspto-grants-2003_08
Patent number
US06605628B1

Reaction notes

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