1,2-Dibromoethane → HCID 58960092, compound

HRID 916155Notes

Reaction equation

HRID 916155 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9](=[O:34])[CH:10]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.[Br:35][CH2:36][CH2:37]Br>C(#N)C>[CH3:7][O:8][C:9](=[O:34])[CH:10]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:37][CH2:36][Br:35])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 16639012HCID 16639012, compound

Product 1

HCID 58960092HCID 58960092, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of potassium carbonate (2 kg) in acetonitrile (5000 ml) is added 2-((2-benzoylphenyl)amino)-3-(4-hydroxyphenyl)-propionic acid methyl ester (555 g, 1.48 mol) and 1,2-dibromoethane (1000 ml). Then the mixture is stirred at room temperature for 24 hours. After that, the reaction mixture is filtered, and then the filtrate is evaporated under a vacuum. The crude product is purified by silica gel chromatography using hexane/EtOAc (4:1) as eluent to give 2-((2-benzoylphenyl)amino)-3-[4-(2-bromoethoxy)-phenyl]-propionic acid methyl ester (442 g, 62%).

Workup

  1. filtrationAfter that, the reaction mixture is filtered
  2. customthe filtrate is evaporated under a vacuum
  3. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-2a8341a1289340458da989861aacd587
Source dataset
uspto-grants-2007_09
Patent number
US07268157B2

Reaction notes

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