Tetrabutylammonium Fluoride → 1,3,5-Trichloro-2-ethynylbenzene

HRID 735086Notes

Reaction equation

HRID 735086 reaction equation
C1([Si](C2C=CC=CC=2)(C2C=CC=CC=2)[C:8]#[C:9][C:10]2[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[CH:12][C:11]=2[Cl:18])C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:16][C:15]1[CH:14]=[C:13]([Cl:17])[CH:12]=[C:11]([Cl:18])[C:10]=1[C:9]#[CH:8]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86060684Triphenyl-(2,4,6-trichlorophenylethynyl)silane

Product 1

HCID 193780291,3,5-Trichloro-2-ethynylbenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A reaction mixture of 5 g (10.8 mmol) of triphenyl-(2,4,6-trichlorophenylethynyl)silane and 4.2 g (16.2 mmol) of tetrabutylammonium fluoride in 50 mL of absolute THF is stirred for half an hour at ambient temperature and then evaporated down. The residue is taken up in diethyl ether and water and extracted. The organic phase is dried over sodium sulfate. The purification is carried out by column chromatography on silica gel (eluant: petroleum ether/toluene (9:1)). Yield: 0.46 g (20.7% of theory); Rf value: 0.6 (silica gel, petroleum ether/toluene (9:1)).

Workup

  1. customevaporated down
  2. extractionwater and extracted
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customThe purification

Sources & evidence

ORD record
ord-427c66677cd246d5bb7cf7e5312da80a
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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