Hydrochloric Acid → 3-(2-fluorophenoxy)propanoic Acid

HRID 600420Notes

Reaction equation

HRID 600420 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].Br[CH2:10][CH2:11][C:12]([OH:14])=[O:13].[OH-].[Na+].Cl>O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 97072-FluorophenolHCID 115533-Bromopropionic acidHCID 14798Sodium Hydroxide

Product 1

HCID 15457213-(2-fluorophenoxy)propanoic AcidYield 38.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-fluorophenol (1) (15 g), 3-bromopropanoic acid (20 g) and NaOH (11 g) was refluxed in 50 mL of water. The solution was cooled to room temperature and acidified to pH 2 with 3 M HCl. The resulting precipitate was isolated by filtration to yield 9.27 g of title compound as a white solid. The filtrate was extracted three times with EtOAc to yield 2.5 g of less pure compound (2).

Workup

  1. customThe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-bc13c27c79814f24a8190b369259546e
Source dataset
uspto-grants-2011_03
Patent number
US07902187B2

Reaction notes

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