Phenylacetylene → 1-fluoro-4-(1-octynyl)benzene

HRID 2213966Notes

Reaction equation

HRID 2213966 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]C.C1(C#C)C=CC=CC=1.[F:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#N)=[CH:20][CH:19]=1>C(#N)C1C=CC=CC=1>[F:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[C:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 10821PhenylacetyleneHCID 123701-OctyneHCID 145174-Fluorobenzonitrile

Product 1

HCID 108997311-fluoro-4-(1-octynyl)benzeneYield 67%

Reagents, catalysts & solvents 1

HCID 7505BenzonitrileSolvent

Procedure

The procedure was identical to Example 2, with the exception that 1-octyne (0.590 ml; 0.441 g; 4.00 mmol) was used as a substrate instead of phenylacetylene and 4-fluorobenzonitrile (0.242 g; 2.00 mmol) was used as a substrate instead of benzonitrile. GC analysis of the organic phase of the hydrolyzed reaction sample after 45 h at 65° C. showed the presence of 1.34 mmol (67% yield) of 1-fluoro-4-(1-octynyl)benzene and no remaining 4-fluorobenzonitrile in the reaction mixture.

Sources & evidence

ORD record
ord-da53e74c167b43d482bb343abe71cd84
Source dataset
uspto-grants-2006_09
Patent number
US07105707B2

Reaction notes

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