2-Bromophenol → 3-(2-Bromophenoxy)propanoic acid

HRID 2173253Notes

Reaction equation

HRID 2173253 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[OH-].[Na+].Br[CH2:12][CH2:13][C:14]([OH:16])=[O:15]>O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 72442-BromophenolHCID 115533-Bromopropionic acidHCID 14798Sodium Hydroxide

Product 1

HCID 167754543-(2-Bromophenoxy)propanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 2-bromophenol (17.3 g, 100 mmol) in 50 mL of H2O was added NaOH (8 g, 200 mmol), 3-bromopropanoic acid (15.3 g, 100 mmol), and the mixture was stirred at reflux overnight. The reaction solution was diluted with H2O, extracted with EtOAc. The aqueous layer was acidified to pH=1˜2 and extracted with EtOAc. The combined organic phase was washed with brine, dried over anhydrous Na2SO4 and concentrated to afford 3-(2-bromophenoxy)propanoic acid.

Workup

  1. temperatureat reflux overnight
  2. extractionextracted with EtOAc
  3. extractionextracted with EtOAc
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-51b68dcc997d4906ac25dbe84f986cf5
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…