1,2-Dibromoethane → HCID 58960103, compound

HRID 916157Notes

Reaction equation

HRID 916157 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9](=[O:35])[CH:10]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26](=[O:34])[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.[Br:36][CH2:37][CH2:38]Br>C(#N)C>[CH3:7][O:8][C:9](=[O:35])[CH:10]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26](=[O:34])[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:38][CH2:37][Br:36])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 58960099HCID 58960099, compound

Product 1

HCID 58960103HCID 58960103, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of potassium carbonate (2 kg) in acetonitrile (5000 ml) is added 2-[(2-(4-fluorobenzoyl)phenyl)amino]-3-(4-hydroxyphenyl)-propionic acid methyl ester (581 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-(4-fluorobenzoyl)phenyl)amino]-3-[4-(2-bromoethoxy)-phenyl]-propionic acid methyl ester (429 g, 58%).

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-c3758ab6dcad4dffa6215ea4d257544e
Source dataset
uspto-grants-2007_09
Patent number
US07268157B2

Reaction notes

Loading…