Methyl Acrylate → Methyl trans-3-[4-(pentafluorosulfanyl)phenyl]prop-2-enoate

HRID 591360Notes

Reaction equation

HRID 591360 reaction equation
F[B-](F)(F)F.[F:6][S:7]([F:19])([F:18])([F:17])([F:16])[C:8]1[CH:13]=[CH:12][C:11]([N+]#N)=[CH:10][CH:9]=1.[C:20]([O:24][CH3:25])(=[O:23])[CH:21]=[CH2:22]>CCO.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:6][S:7]([F:19])([F:18])([F:17])([F:16])[C:8]1[CH:13]=[CH:12][C:11](/[CH:22]=[CH:21]/[C:20]([O:24][CH3:25])=[O:23])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 7294Methyl AcrylateHCID 1222352754-(Pentafluorosulfanyl)phenyldiazonium Tetrafluoroborate

Product 1

HCID 21576971Methyl trans-3-[4-(pentafluorosulfanyl)phenyl]prop-2-enoate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolvent

Procedure

Diazonium salt 1 reacted with methyl acrylate in the presence of Pd(OAc)2 in 95% EtOH to give methyl trans-3-[4-(pentafluorosulfanyl)phenyl]prop-2-enoate 3 in 85% isolated yield with no cis isomer being observed, as seen in FIG. 2.

Sources & evidence

ORD record
ord-80d2645015354f87977cb496e2204faf
Source dataset
uspto-grants-2016_01
Patent number
US09238660B1

Reaction notes

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