Hydrochloric Acid → 4-Fluoro-3-((trimethylsilyl)ethynyl)aniline

HRID 880151Notes

Reaction equation

HRID 880151 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]#[C:12][Si:13]([CH3:16])([CH3:15])[CH3:14].Cl>CO.[Fe]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:11]#[C:12][Si:13]([CH3:14])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12687357((2-Fluoro-5-nitrophenyl)ethynyl)trimethylsilane

Product 1

HCID 126873584-Fluoro-3-((trimethylsilyl)ethynyl)anilineYield 92.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

460 mg of iron are added to a solution of 460 mg of [(2-fluoro-5-nitrophenyl)ethynyl](trimethyl)silane in 10 ml of methanol, and the medium is adjusted to pH 4-5 with concentrated hydrochloric acid. After refluxing for three and a half hours, the medium is cooled and then filtered through silica, and concentrated to dryness under reduced pressure. The residue is taken up with diethyl ether, the insoluble material is filtered off, and then the filtrate is concentrated to dryness under reduced pressure. 370 mg of 4-fluoro-3-[(trimethylsilyl)ethynyl]aniline are obtained in the form of an orangey oil, the characteristics of which are the following:

Workup

  1. temperatureAfter refluxing for three and a half hours
  2. temperaturethe medium is cooled
  3. filtrationfiltered through silica
  4. concentrationconcentrated to dryness under reduced pressure
  5. filtrationthe insoluble material is filtered off
  6. concentrationthe filtrate is concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6b92bf8df27a48f1882929a9a6f36c83
Source dataset
uspto-grants-2015_03
Patent number
US08993565B2

Reaction notes

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