1-Chloro-2-ethynylbenzene → 1-Chloro-3-(2-chlorophenylethynyl)-5-(3,3-dichloroprop-2-enyloxy)-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]benzene

HRID 497054Notes

Reaction equation

[Cl:1][C:2]1[C:3]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=2)=[C:4](I)[CH:5]=[C:6]([O:8][CH2:9][CH:10]=[C:11]([Cl:13])[Cl:12])[CH:7]=1.[Cl:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]#[CH:38]>C(N(CC)CC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]=[C:11]([Cl:13])[Cl:12])[CH:5]=[C:4]([C:38]#[C:37][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[Cl:30])[C:3]=1[O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Under an atmosphere of protective gas, 0.1 g of 3-chloro-5-(3,3-dichloroprop-2-enyloxy)-1-iodo-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]benzene, 0.03 g of 1-chloro-2-ethynylbenzene and 0.003 g of copper(I) iodide were dissolved in 1 ml of triethylamine. 0.005 g of bis(triphenylphosphine)palladium(II) chloride was added, and the mixture was stirred at 70° C. for 1 hour. The mixture was then allowed to cool and concentrated under reduced pressure, and the resulting residue was subjected to chromatographic purification. Yield: 0.085 g (84%)

Workup

temperatureto cool
concentrationconcentrated under reduced pressure
customthe resulting residue was subjected to chromatographic purification

Sources & evidence

ORD record: ord-92a23c6079f7404a99fb005e93533f0d
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949551B2

Reaction notes

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