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

HRID 1350288Notes

Reaction equation

HRID 1350288 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[CH2:14](I)[CH3:15]>>[CH2:14]([S:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1)[CH3:15]

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-00e2793147ed4df6941b41df779a7213
Source dataset
uspto-grants-2007_05
Patent number
US07214681B2

Reaction notes

Loading…