Benzyl mercaptan → [3-(2-Benzylsulfanylmethyl-4-chloro-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester

HRID 888480Notes

Reaction equation

HRID 888480 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]([Cl:21])=[CH:17][C:16]=2[CH2:22]Br)[CH:7]=1)[CH3:2].[CH2:25]([SH:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[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]([Cl:21])=[CH:17][C:16]=2[CH2:22][S:32][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 58237456[3-(2-Bromomethyl-4-chloro-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester

Product 1

HCID 58372812[3-(2-Benzylsulfanylmethyl-4-chloro-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To [3-(2-bromomethyl-4-chloro-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester (0.15 g, 0.36 mmol) and benzyl mercaptan (0.06 mL, 0.4 mmol) in 1,4-dioxane (10 mL) was added sodium hydride (60% in mineral oil; 0.05 g, 1.25 mmol), and the reaction was stirred for 1 hour at room temperature. After work-up, the crude material was purified by preparative HPLC to give the title compound.

Workup

  1. customAfter work-up, the crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-30ed10fc8e714d74941d00cc7cdc0f46
Source dataset
uspto-grants-2012_08
Patent number
US08247602B2

Reaction notes

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