Chloroacetic Acid → 2-(2-Acetyl-4-bromophenoxy)acetic acid

HRID 525144Notes

Reaction equation

HRID 525144 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.Cl[CH2:13][C:14]([OH:16])=[O:15].[OH-].[Na+]>O>[C:8]([C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[O:11][CH2:13][C:14]([OH:16])=[O:15])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 14798Sodium HydroxideHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 192613632-(2-Acetyl-4-bromophenoxy)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 1-(5-bromo-2-hydroxyphenyl)ethanone (9.53 mmol) in water (70 mL) was treated with chloroacetic acid (11.64 mmol) and a solution of NaOH (21.25 mmol) in water (20 mL). The resulting yellow suspension was flushed with N2 and stirred at reflux overnight. Analysis by LCMS indicated the consumption of starting material and desired product formation. The reaction was cooled to room temperature and then acidified to pH˜3 with 1N aq HCl. The mixture was then cooled to 0° C. resulting in precipitate formation. A grey sticky solid was filtered and used without further purification. MS(ES)+ m/e 273/275 [M+H]+ (bromide isotope pattern).

Workup

  1. customThe resulting yellow suspension was flushed with N2
  2. temperatureat reflux overnight
  3. customthe consumption of starting material and desired product formation
  4. temperatureThe mixture was then cooled to 0° C.
  5. customresulting in precipitate formation
  6. filtrationA grey sticky solid was filtered
  7. customused without further purification

Sources & evidence

ORD record
ord-354e11f1fb0b45a3a03f23def3a8f90a
Source dataset
uspto-grants-2016_05
Patent number
US09340529B2

Reaction notes

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