Bromoacetic Acid → 4-Chloro-2-benzoylphenoxyacetic acid

HRID 583227Notes

Reaction equation

HRID 583227 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:3]=1.[H-].[Na+].Br[CH2:20][C:21]([OH:23])=[O:22]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:20][C:21]([OH:23])=[O:22])=[C:4]([C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 6227Bromoacetic AcidHCID 6799Chlorohydroxy benzophenoneHCID 24758Sodium hydride

Product 1

HCID 100628354-Chloro-2-benzoylphenoxyacetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-2-benzoylphenol (1.95 g) in DMF (30 ml) was added sodium hydride (60% oil) (400 mg). The mixture was stirred for 30 minutes at room temperature, to which was then added methyl ester of bromoacetic acid (1.0 ml). The mixture was stirred for 2 hours under cooling with ice-water. The reaction mixture was concentrated, to which was added ethyl acetate. The mixture was washed with water, which was then dried. The solvent was distilled off, and the residue was purified by means of a silica gel (40 g) column chromatography (hexane-ethyl acetate=3:1) to afford methyl ester of 4-chloro-2-benzoylphenoxyacetic acid as colorless crystals (2.21 g).

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. concentrationThe reaction mixture was concentrated, to which
  3. additionwas added ethyl acetate
  4. washThe mixture was washed with water, which
  5. customwas then dried
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by means of a silica gel (40 g) column chromatography (hexane-ethyl acetate=3:1)

Sources & evidence

ORD record
ord-3d728850475a4b79b6cbcaa6d0fd9dfe
Source dataset
uspto-grants-1999_07
Patent number
US05929107

Reaction notes

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