Trimethylsilylacetylene → 1-Chloro-3-ethynyl-2-fluorobenzene

HRID 59265Notes

Reaction equation

HRID 59265 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[C:3]=1[F:9].[C:10]([Si](C)(C)C)#[CH:11].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]=[CH:6][CH:5]=[C:4]([C:10]#[CH:11])[C:3]=1[F:9]

Participants

7

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 2724141Tetrabutylammonium FluorideHCID 27782191-Chloro-2-fluoro-3-iodobenzene

Product 1

HCID 630334871-Chloro-3-ethynyl-2-fluorobenzeneYield 82.9%

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 1-chloro-2-fluoro-3-iodobenzene (1.0 g, 3.9 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 0.500 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 4.66 (s, 1H), 7.25 (t, J=8.4 Hz, 1H), 7.54 (t, J=7.2 Hz, 1H), 7.65 (t, J=7.8 Hz, 1H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-3374171ece924f449476c7ff82ea4c35
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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