Propargyl bromide → HCID 22159639, compound

HRID 1089599Notes

Reaction equation

HRID 1089599 reaction equation
[F:1][C:2]([F:23])([Cu])[C:3]([F:21])([F:20])[C:4]([F:19])([F:18])[C:5]([F:17])([F:16])[C:6]([F:15])([F:14])[C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[F:9].[CH2:24](Br)[C:25]#[CH:26]>>[F:1][C:2]([F:23])([CH:24]=[C:25]=[CH2:26])[C:3]([F:21])([F:20])[C:4]([F:19])([F:18])[C:5]([F:17])([F:16])[C:6]([F:15])([F:14])[C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[F:9]

Participants

3

Reactant 2

HCID 7842Propargyl bromideHCID 178506338HCID 178506338, compound

Product 1

HCID 22159639HCID 22159639, compoundYield 10%

Procedure

L. Coe and N. E. Milner, Journal of Organometallic Chemistry, 70, 147(1974) disclosed the reaction of perfluoro-n-heptyl copper with propargyl bromide at 110° C. to be an extremely violent exothermic reaction that afforded, after a difficult workup that included a minor explosion, a 10% yield of 1-(perfluoro-n-heptyl)-1,2-propadiene. There is no disclosure nor suggestion relating to a means of performing said conversion in a safe, controllable, reproducible, high-yield manner.

Workup

  1. customan extremely violent exothermic reaction
  2. customthat afforded

Sources & evidence

ORD record
ord-1ef29e294b8d43549ea7696bb4d018a2
Source dataset
uspto-grants-1990_10
Patent number
US04967022

Reaction notes

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