Iodoethane → Ethyl 2-(4-(ethylthio)phenyl)acetate

HRID 729695Notes

Reaction equation

HRID 729695 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][CH:7]=1)[CH3:2].[CH2:14](I)[CH3:15]>>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:14][CH3:15])=[CH:8][CH:7]=1)[CH3:2]

Participants

3

Reactant 2

HCID 6340IodoethaneHCID 123300434-Mercapto-phenyl-acetic acid ethyl ester

Product 1

HCID 82553740Ethyl 2-(4-(ethylthio)phenyl)acetate

Procedure

Alkylation of ethyl(4-mercaptophenyl)acetate (20 g, 102 mmol) with EtI (9.8 mL, 122 mmol), using a similar procedure to that described in Preparation 39, furnished ethyl(4-ethylsulfanylphenyl)acetate: m/z (ES+)=225.2 [M+H]+. Oxidation of this compound (22.6 g, 101 mmol) with mCPBA (222 mmol), employing a protocol similar to that described in Preparation 22, provided the title compound: m/z (ES+)=298.2 [M+MeCN+H]+.

Workup

  1. customthat described in Preparation 39

Sources & evidence

ORD record
ord-bbfed2cb6bc944bd8c2522b18ed2f7fa
Source dataset
uspto-grants-2009_09
Patent number
US07582632B2

Reaction notes

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