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

HRID 1837531

Reaction equation

HRID 1837531 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-f323ca28428c4bb2907b98a8f7517818
Source dataset
uspto-grants-2004_08
Patent number
US06784184B2

Linked notes

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