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

HRID 490953

Reaction equation

HRID 490953 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-8e3df580c6a841e6a6a0593fac2ce51a
Source dataset
uspto-grants-2009_05
Patent number
US07528250B2

Linked notes

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