Tetrabutylammonium Fluoride → 1-Fluoro-4-(hexa-1,5-diynyl)benzene
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (6-(4-fluorophenyl)hexa-1,5-diynyl)trimethylsilane (1.90 g, 7.7 mmol) in THF (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 2h30. 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
- temperaturewarmed to room temperature for 2h30
- customThe reaction was quenched with water
- extractionthe aqueous layer was extracted with diethyl ether
- washThe organic layer was washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe product was purified by flash chromatography (prepacked 25 g silicagel column, DCM 100% as eluent)
Sources & evidence
- ORD record
- ord-48804bee3474439d800ea017ff0a6a44
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08674106B2
Reaction notes
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