2-Propanethiol → [3-(4-Bromo-2-isopropylsulfanylmethyl-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester

HRID 888494Notes

Reaction equation

HRID 888494 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[CH2:22]Br)[CH:7]=1)[CH3:2].[CH3:25][CH:26]([SH:28])[CH3:27].[H-].[Na+]>O1CCOCC1>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[CH2:22][S:28][CH:26]([CH3:27])[CH3:25])[CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 63642-PropanethiolHCID 24758Sodium hydrideHCID 58237498[3-(4-Bromo-2-bromomethyl-phenoxy)-4-methoxy-phenyl]acetic acid ethyl ester

Product 1

HCID 58372820[3-(4-Bromo-2-isopropylsulfanylmethyl-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To [3-(4-bromo-2-bromomethyl-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester and 2-propanethiol in 1,4-dioxane was added sodium hydride (60% in mineral oil), and the reaction was stirred for 1 hour at room temperature. After work-up, the crude material was purified by silica gel chromatography (0-20% EtOAc in hexanes) to give the title compound.

Workup

  1. customAfter work-up, the crude material was purified by silica gel chromatography (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-67dede9a54b54040ae905fe033b91377
Source dataset
uspto-grants-2012_08
Patent number
US08247602B2

Reaction notes

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