Triphenylphosphine → ((2-Fluoro-5-nitrophenyl)ethynyl)trimethylsilane

HRID 880150Notes

Reaction equation

HRID 880150 reaction equation
[C:1]([Si:3]([CH3:6])([CH3:5])[CH3:4])#[CH:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:27]1[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:28]=1[F:36]>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:36][C:28]1[CH:29]=[CH:30][C:31]([N+:33]([O-:35])=[O:34])=[CH:32][C:27]=1[C:2]#[C:1][Si:3]([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 696992-Bromo-1-fluoro-4-nitrobenzene

Product 1

HCID 12687357((2-Fluoro-5-nitrophenyl)ethynyl)trimethylsilane

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

1.126 ml of ethynyl(trimethyl)silane, 55 mg of triphenylphosphine and 24 mg of palladium (2+) acetate are added to a solution of 1.169 g of 2-bromo-1-fluoro-4-nitrobenzene in 13 ml of triethylamine with stirring and under argon. After four and a half hours at a temperature of 100° C., the reaction medium is cooled and the insoluble material is filtered off through sintered glass. The filtrate is concentrated to dryness under reduced pressure. After two silica column purifications, eluent: 90/10 heptane/EtOAc then 955 heptane/EtOAc, 460 mg of [(2-fluoro-5-nitrophenyl)ethynyl](trimethyl)silane are obtained in the form of a yellow solid, the characteristics of which are the following:

Workup

  1. waitAfter four and a half hours at a temperature of 100° C.
  2. temperaturethe reaction medium is cooled
  3. filtrationthe insoluble material is filtered off through sintered glass
  4. concentrationThe filtrate is concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-431e834e42f9488eacff8660e8a9c80d
Source dataset
uspto-grants-2015_03
Patent number
US08993565B2

Reaction notes

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