Tetrahydrofuran → 1-Fluoro-4-(hexa-1,5-diynyl)benzene

HRID 422282Notes

Reaction equation

HRID 422282 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][CH2:11][C:12]#[C:13][Si](C)(C)C)=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][CH2:11][C:12]#[CH:13])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 66597810(6-(4-Fluorophenyl)hexa-1,5-diynyl)trimethylsilane

Product 1

HCID 860867911-Fluoro-4-(hexa-1,5-diynyl)benzeneYield 45%

Conditions

Temperature
0 °C

Procedure

To a solution of (6-(4-fluorophenyl)hexa-1,5-diynyl)trimethylsilane (1.90 g, 7.7 mmol) in TH F (24 mL) cooled in a ice bath at 0° C., was added dropwise 7.7 mL of tetrabutylammonium fluoride 1M in THF solution (7.70 mmol). The reaction mixture was stirred 15 min at 0° C., and warmed to room temperature for 2 h 30. The reaction was quenched with water and the aqueous layer was extracted with diethyl ether. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The product was purified by flash chromatography (prepacked 25 g silicagel column, DCM 100% as eluent) to afford 500 mg of 1-fluoro-4-(hexa-1,5-diynyl)benzene (Yield: 45%) as a yellow oil.

Workup

  1. temperaturewarmed to room temperature for 2 h 30
  2. customThe reaction was quenched with water
  3. extractionthe aqueous layer was extracted with diethyl ether
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by flash chromatography (prepacked 25 g silicagel column, DCM 100% as eluent)

Sources & evidence

ORD record
ord-2ecf01d8633544d8b98811103d102f56
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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