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

HRID 1582954Notes

Reaction equation

HRID 1582954 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 In the manner described in Example 30, above, the following alcohols in Table III were converted to the corresponding bromides:

Workup

  1. customThis was chromatographed on silica gel with hexane

Sources & evidence

ORD record
ord-d58c9f81ad114ae2b90dbe6f42048d1a
Source dataset
uspto-grants-2004_05
Patent number
US06740675B2

Reaction notes

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