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

HRID 982741

Reaction equation

HRID 982741 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-bf4b29bf5f514b219217fe33e405e049
Source dataset
uspto-grants-2005_03
Patent number
US06861445B2

Linked notes

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