Benzyl Bromide → HCID 59496817, compound

HRID 417016Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:37])[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:21][C:22]2[CH:27]=[C:26]([OH:28])[CH:25]=[C:24]([Br:29])[CH:23]=2)[C:10]=1[CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH3:2].[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH2:1]([O:3][C:4](=[O:37])[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:21][C:22]2[CH:23]=[C:24]([Br:29])[CH:25]=[C:26]([O:28][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:27]=2)[C:10]=1[CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH3:2]

Participants

Reactant 3

HCID 7498Benzyl Bromide

HCID 11430Potassium Carbonate

HCID 59496799HCID 59496799, compound

Product 1

HCID 59496817HCID 59496817, compoundYield 98.9%

Procedure

A similar procedure as described in Example 43, step 3 was used, starting from 4-[3-[6-(3-bromo-5-hydroxy-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (930 mg, 1.6 mmol), benzyl bromide (343 mg, 2.0 mmol), and potassium carbonate (553 mg, 4.0 mmol) to afford 4-[3-[6-(3-benzyloxy-5-bromo-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (1.06 g, 98%) as a colorless viscous oil: ES(+)-HRMS m/e calcd for C36H45BrO7 (M+Na)+ 691.2241. found 691.2238.

Sources & evidence

ORD record: ord-9f2ce82e09ca418888751722a66871ef
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088936B2

Reaction notes

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