1,2-Dibromoethane → HCID 58960102, compound

HRID 916160Notes

Reaction equation

HRID 916160 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5](=[O:34])[CH:6]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[O:33])[C:23]1[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[Br:35][CH2:36][CH2:37]Br>C(O)C>[CH3:3][O:4][C:5](=[O:34])[CH:6]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[O:33])[C:23]1[CH:28]=[CH:27][C:26]([C:29]([CH3:30])([CH3:31])[CH3:32])=[CH:25][CH:24]=1)[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:37][CH2:36][Br:35])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 14797Potassium HydroxideHCID 58960084HCID 58960084, compound

Product 1

HCID 58960102HCID 58960102, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of potassium hydroxide (0.17 g, 2.95 mmol) in ethanol (20 ml) is added 2-[(2-(4-tert-butylbenzoyl)phenyl)amino]-3-(4-hydroxyphenyl)-propionic acid methyl ester (1.27 g, 2.95 mmol) and 1,2-dibromoethane (5.54 g, 29.50 mmol). Then the mixture is heated to reflux for 8 hours. After cooled, the reaction mixture is filtered to remove the solid formed, 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 the title compound (0.67 g, 42%).

Workup

  1. temperatureThen the mixture is heated
  2. temperatureto reflux for 8 hours
  3. temperatureAfter cooled
  4. filtrationthe reaction mixture is filtered
  5. customto remove the solid
  6. customformed
  7. customthe filtrate is evaporated under a vacuum
  8. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-69f4e14aac1a4fb19eca1060af0ca4c8
Source dataset
uspto-grants-2007_09
Patent number
US07268157B2

Reaction notes

Loading…