Trimethylsilylacetylene → HCID 15405429, compound

HRID 1018401Notes

Reaction equation

HRID 1018401 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([O:9][CH3:10])[CH:3]=1.[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13]>CNC.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.[Cu]I>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:16]#[C:15][Si:12]([CH3:14])([CH3:13])[CH3:11])=[CH:3][C:4]=1[O:9][CH3:10]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 136049094-Bromo-1-fluoro-2-methoxybenzene

Product 1

HCID 15405429HCID 15405429, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 674DimethylamineSolvent

Procedure

4-Bromo-2-methoxyfluorobenzene (obtainable from 5-bromo-2-fluorophenol by reaction with dimethyl sulfate under basic conditions) is reacted with trimethylsilylacetylene with catalysis by bis(triphenylphosphine)palladium(II) chloride and copper(I) iodide in dimethylamine at 20° C. to give 1-(4-fluoro-3-methoxyphenyl)-2-(trimethylsilyl)ethyne; after filtration chromatography (SiO2/dichloromethane), the crude product is stirred in methanol for 1 hour at 20° C. with addition of 1 N aqueous NaOH solution. Removal of the solvent by distillation and chromatography (SiO2/dichloromethane) gives 4-ethynyl-3-methoxyfluorobenzene.

Sources & evidence

ORD record
ord-d29991512cb644178c71ed074e092763
Source dataset
uspto-grants-2002_11
Patent number
US06482478B1

Reaction notes

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