Triethylamine → Tert-butyl-(3-chlorobiphenyl-4-ylethynyl)dimethylsilane

HRID 735061Notes

Reaction equation

HRID 735061 reaction equation
[Si:1]([C:8]#[CH:9])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].FC(F)(F)S(O[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][C:17]=1[Cl:28])(=O)=O.C(N(CC)CC)C>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[C:4]([Si:1]([C:8]#[C:9][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][C:17]=1[Cl:28])([CH3:3])[CH3:2])([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 2757281(tert-Butyldimethylsilyl)acetyleneHCID 180010793-Chlorobiphenyl-4-yl trifluoromethanesulfonate

Product 1

HCID 68816298Tert-butyl-(3-chlorobiphenyl-4-ylethynyl)dimethylsilane

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

0.84 g (1.2 mmol) of bis-(triphenylphosphine)palladium (II) chloride, 0.23 g (1.2 mmol) of copper (I) iodide, and 6.28 mL (33.6 mmol) of (tert-butyldimethylsilyl)acetylene is added under an argon atmosphere to a solution of 8.1 g (24 mmol) of 3-chlorobiphenyl-4-yl trifluoromethanesulfonate in 50 mL of absolute DMF and 13.31 mL (96 mmol) of triethylamine.

Sources & evidence

ORD record
ord-ef609e1871c64a76a13ef6d6e918cd23
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

Loading…