3-Fluorophenol → 3-(3-Fluorophenoxy)propanoic acid

HRID 2356970Notes

Reaction equation

HRID 2356970 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[CH2:10][CH2:11][C:12]([OH:14])=[O:13].[OH-].[Na+]>O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 97433-FluorophenolHCID 115533-Bromopropionic acidHCID 14798Sodium Hydroxide

Product 1

HCID 150860153-(3-Fluorophenoxy)propanoic acidYield 31.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Fluorophenol (8.9 g, 79.5 mmol) and 3-bromopropionic acid (12.24 g, 80.0 mmol) were placed in a flask. A solution of NaOH (6.7 g, 167 mmol) in 20 mL water was added slowly to the flask. The reaction mixture was heated to reflux for two hours and then cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was dried over MgSO4, and solvent was evaporated under reduced pressure to give 4.57 g (25 mmol, 31.4%) of 3-(3-fluoro-phenoxy)-propionic acid. MS: 185 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for two hours
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over MgSO4, and solvent
  5. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-5f91fe69cad04cb687e0ea50ada091ba
Source dataset
uspto-grants-2010_07
Patent number
US07759389B2

Reaction notes

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