Trimethylsilylacetylene → 2-Chloro-1-ethynyl-4-(trifluoromethyl)benzene

HRID 59266Notes

Reaction equation

HRID 59266 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1I.[C:13]([Si](C)(C)C)#[CH:14].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[Cu](I)I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:13]#[CH:14]

Participants

7

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 2724141Tetrabutylammonium FluorideHCID 27366123-Chloro-4-iodobenzotrifluoride

Product 1

HCID 636689832-Chloro-1-ethynyl-4-(trifluoromethyl)benzeneYield 80.2%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in step-5 and step-6 of Intermediate-2 by using 2-chloro-1-iodo-4-(trifluoromethyl)benzene (1.0 g, 3.2 mmol), ethynyl(trimethyl)silane (0.541 g, 5.5 mmol), copper iodide (0.027 g, 0.14 mmol), bis(triphenylphosphine) palladium(II) chloride (0.050 g, 0.072 mmol), TBAF (catalytic) and DCM to afford 0.525 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 4.88 (s, 1H), 7.73 (d, J=8.4 Hz, 1H), 7.83 (d, J=7.8 Hz, 1H), 8.01 (s, 1H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-ffa5824dad7e47baabc1c01045922318
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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