4-Bromothiophenol → HCID 10640226, compound

HRID 491015Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Br[C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 660494-Bromothiophenol

HCID 90290tert-Butyl 2-bromo-2-methylpropionate

Product 1

HCID 10640226HCID 10640226, compoundYield 80%

Procedure

As above, tert-butyl 2-[4-(2-aminoethyl)phenylthio]-2-methylpropionate was obtained in 86% yield by reacting 4-bromothiophenol (1) as a starting material with tert-butyl 2-bromoisobutyrate to obtain tert-butyl 2-(4-bromophenylthio)-2-methylpropionate (2) in 80% yield, reacting it with N-vinyl phthalimide in presence of palladium catalyst for 24 hours to obtain tert-butyl 2-[4-(2-phthalimidoethenyl)phenylthio]-2-methylpropionate (3) in 84% yield, reducing the resulted compound (3) under Wilkinson catalyst to obtain tert-butyl 2-[4-(2-phthalimidoethyl)phenylthio]-2-methylpropionate (4) in 91% yield and then reacting the resulted compound (4) with hydrazine.

Sources & evidence

ORD record: ord-0527445de36b43edbd9f69d44f96a33a
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528276B2

Reaction notes

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