Hydrochloric Acid → 3-(2-Bromo-4,5-difluorophenoxy)propanoic acid

HRID 1363193Notes

Reaction equation

HRID 1363193 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([F:11])=[CH:6][C:5]=1[OH:12].Br[CH2:14][CH2:15][C:16]([OH:18])=[O:17].Cl>O>[Br:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([F:11])=[CH:6][C:5]=1[O:12][CH2:14][CH2:15][C:16]([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 115533-Bromopropionic acidHCID 14798Sodium HydroxideHCID 27362882-Bromo-4,5-difluorophenol

Product 1

HCID 669704713-(2-Bromo-4,5-difluorophenoxy)propanoic acidYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 1.68 g of NaOH (42 mmol) in 5 mL of water was added slowly to the suspension of 2.29 mL (20 mmol) 2-bromo-4,5-difluorophenol and 3.07 g (20 mmol) 3-bromopropionic acid. The mixture was heated at 100° C. in an oil bath for 5 hours, and then allowed to cool to room temperature. Water was added to completely dissolve any solid material and the reaction mixture was made acidic with concentrated HCl. The product was extracted into ether (3 times), and the combined organic layers was dried over Na2SO4 and evaporated to give 3.7 g (66%) of the title compound as a light brown solid. 1H NMR (300 MHz, CDCl3): δ 7.4 (t, 1H), 6.8 (q, 1H), 4.3 (t, 2H), 2.9 (t, 2H).

Workup

  1. temperatureto cool to room temperature
  2. dissolutionto completely dissolve any solid material
  3. extractionThe product was extracted into ether (3 times)
  4. dry with materialthe combined organic layers was dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-60e853fb7e654056ba69a9ba2409c65e
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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