Water → 3-(4-Bromo-2-trifluoromethoxyphenyl)propanoic acid

HRID 1984910Notes

Reaction equation

HRID 1984910 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[C:4]([O:12][C:13]([F:16])([F:15])[F:14])[CH:3]=1.CC(C)=[O:19].OS(O)(=O)=O.O=[Cr](=O)=O.O>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:19])=[O:11])=[C:4]([O:12][C:13]([F:14])([F:15])[F:16])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 689163273-(4-Bromo-2-trifluoromethoxy-phenyl)-propan-1-olHCID 131709961Jones' reagent

Product 1

HCID 688476333-(4-Bromo-2-trifluoromethoxyphenyl)propanoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-(4-bromo-2-trifluoromethoxy-phenyl)-propan-1-ol obtained in step B of example 62 (1 g, 3.34 mmol) in acetone (15 mL) was added Jones reagent (4 mL) at 4° C. The mixture was stirred at ambient temperature for 2 hr. The solution was poured into water (50 mL), and the aqueous layer was extracted with Et2O (three times). The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by flash chromatography (silica gel, 25% EtOAc in hexane) to give 3-(4-Bromo-2-trifluoromethoxy-phenyl)-propionic acid (930 mg, 89%) as a colorless oil.

Workup

  1. extractionthe aqueous layer was extracted with Et2O (three times)
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography (silica gel, 25% EtOAc in hexane)

Sources & evidence

ORD record
ord-5684100c154141d7ae831e4382ef46e0
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

Loading…