Bromoethene → 5-Ethenyl-1,2,3-trifluorobenzene

HRID 1757341Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].[Li][CH2:12][CH2:13]CC.C(Br)=C>C1COCC1.[Br-].[Zn+2].[Br-].[Ni](Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH2:13])[CH:5]=[C:6]([F:9])[C:7]=1[F:8]

Participants

Conditions

Temperature: -65 °C

Procedure

A mixture of 1 mol of 3,4,5-trifluorobromobenzene and 3 l of THF is admixed at -70° C. with 1 mol of BuLi. Subsequently, a mixture of 0.5 mol of zinc bromide in 1 l of THF is added to the reaction mixture, and this mixture is stirred for 30 minutes at -65° C. Then 1 mol of vinyl bromide and 0.022 mol of nickel(II) chloride/TPP is added.

Workup

additionis added to the reaction mixture

Sources & evidence

ORD record: ord-ae280176e84e4338bb2ad0ef6dbd4031
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05445764

Reaction notes

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