Potassium Carbonate → 4-[3-[6-(3-Acetyl-5-bromo-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

HRID 417031Notes

Reaction equation

HRID 417031 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].[Br:30][C:31]1[CH:32]=[C:33]([C:38](=[O:40])[CH3:39])[CH:34]=[C:35]([OH:37])[CH:36]=1.C(=O)([O-])[O-].[K+].[K+]>>[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:37][C:35]2[CH:36]=[C:31]([Br:30])[CH:32]=[C:33]([C:38](=[O:40])[CH3:39])[CH:34]=2)[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:2]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 575864914-[3-(6-Bromo-hexyl)-2-(ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl esterHCID 594968071-(3-Bromo-5-hydroxyphenyl)ethanone

Product 1

HCID 594968364-[3-[6-(3-Acetyl-5-bromo-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl esterYield 79.3%

Procedure

A similar procedure as described in Example 43, step 3 was used, starting from 4-[3-[6-bromo-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (2.36 g, 5.0 mmol), 1-(3-bromo-5-hydroxy-phenyl)-ethanone (965 mg, 4.48 mmol), and potassium carbonate (1.38 g, 10 mmol) to afford 4-[3-[6-(3-acetyl-5-bromo-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (2.15 g, 79%) as a colorless viscous oil: EI(+)-HRMS m/e calcd for C31H41BrO7 (M+Na)+ 627.1928. found 627.1925.

Sources & evidence

ORD record
ord-b44432aeefc74254a96b92e42059ed1f
Source dataset
uspto-grants-2012_01
Patent number
US08088936B2

Reaction notes

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