4-Fluorophenol → 3-(4-Fluorophenoxy)propionic acid

HRID 1704138Notes

Reaction equation

HRID 1704138 reaction equation
[H-].[Na+].Br[CH:4]([CH3:8])[C:5]([OH:7])=[O:6].[F:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1>COCCOC>[F:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:4]([CH3:8])[C:5]([OH:7])=[O:6])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 117292-Bromopropionic acidHCID 24758Sodium hydride

Product 1

HCID 38721403-(4-Fluorophenoxy)propionic acidYield 60.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

To a stirred slurry of 8.3 g of sodium hydride (57° 10 NaH in oil) in 100 ml of dry 1,2-dimethoxyethane at 5° C. is added 15.3 g of 2-bromopropionic acid in 50 ml of 1,2-dimethoxyethane and 10.5 g of 4-fluorophenol in 50 ml of 1,2-dimethoxyethane. The mixture is refluxed for 6 hrs, cooled and filtered. The solid is partitioned between dichloromethane and 1N HCl. The organic layer is dried (MgSO4) and concentrated to 50 ml. The mixture is filtered to give 10.4 g of product, mp 113°-115° C.

Workup

  1. temperatureThe mixture is refluxed for 6 hrs
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe solid is partitioned between dichloromethane and 1N HCl
  5. dry with materialThe organic layer is dried (MgSO4)
  6. concentrationconcentrated to 50 ml
  7. filtrationThe mixture is filtered

Sources & evidence

ORD record
ord-f425f52853524295a7a6ffdc94772be3
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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