3-Iodo-5-nitrophenol → 4-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(3-iodo-5-nitro-phenoxy)-hexyl]-phenoxy}-butyric acid ethyl ester

HRID 420385Notes

Reaction equation

HRID 420385 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br)[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:2].[I:30][C:31]1[CH:32]=[C:33]([OH:40])[CH:34]=[C:35]([N+:37]([O-:39])=[O:38])[CH:36]=1>>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:40][C:33]2[CH:34]=[C:35]([N+:37]([O-:39])=[O:38])[CH:36]=[C:31]([I:30])[CH:32]=2)[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:2]

Participants

3

Reactant 2

HCID 184199793-Iodo-5-nitrophenolHCID 575864914-[3-(6-Bromo-hexyl)-2-(ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

Product 1

HCID 575864524-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(3-iodo-5-nitro-phenoxy)-hexyl]-phenoxy}-butyric acid ethyl esterYield 73.3%

Procedure

A similar procedure as described in Example 12, step 7 was used, starting from 4-[3-(6-bromo-hexyl)-2-(ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (9.39 g, 19.92 mmol) and 3-iodo-5-nitro-phenol (4.8 g, 18.11 mmol) to afford 4-{2-(2-ethoxycarbonyl-ethyl)-3-[6-(3-iodo-5-nitro-phenoxy)-hexyl]-phenoxy}-butyric acid ethyl ester (8.7 g, 73%) as a light yellow oil: ES(+)-HRMS m/e calculated for C29H38INO8 (M+H)+ 656.1715, found 656.1721.

Sources & evidence

ORD record
ord-a4c6c84132e34c71b3ba587eaba2017f
Source dataset
uspto-grants-2012_01
Patent number
US08093385B2

Reaction notes

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