2,6-Dichlorobenzoic acid → 2,6-Dichlorobenzoxymethylketone

HRID 446896

Reaction equation

HRID 446896 reaction equation
Br[CH2:2][C:3]([CH2:5]Br)=[O:4].[Cl:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:9]=1[C:10](O)=[O:11].[F-].[K+]>CN(C)C=O>[Cl:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:9]=1[CH2:10][O:11][CH2:2][C:3]([CH2:5][O:11][CH2:10][C:9]1[C:8]([Cl:7])=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:17])=[O:4]

Participants

5

Reactant 3

HCID 57582,6-Dichlorobenzoic acidHCID 699521,3-Dibromo-2-propanoneHCID 522689Potassium Fluoride

Product 1

HCID 571166882,6-Dichlorobenzoxymethylketone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The bromomethylketone derivative (4.36 g) and 2,6-dichlorobenzoic acid (2.28 g, 1.1 eq) were dissolved in dimethylformamide (18 mL), KF (1.58 g, 2.5 eq) was added thereto, and the mixture was stirred for 2 h at room temperature. The residue obtained by concentration under reduced pressure was extracted with ethyl acetate, washed with water, twice with saturated aqueous sodium hydrogen carbonate solution, and aqueous sodium chloride solution, dried (anhydrous Na2SO4), and concentrated under reduced pressure to give the 2,6-dichlorobenzoxymethylketone derivative. This compound was dissolved in methanol (20 mL), and reacted by adding NaBH4 (412 mg)-methanol solution (40 mL). The reaction mixture was slowly warmed to room temperature for 2 h. The reaction was stopped by acetic acid. The reaction mixture was distilled under reduced pressure to remove methanol, extracted with ethyl acetate (50 mL×2), washed with water and aqueous sodium chloride solution, dried (anhydrous Na2SO4), concentrated under reduced pressure, and separated by column chromatography (ethyl acetate-hexane, 1:5) to give 4.80 g (86%) of the title compound.

Workup

  1. customThe residue obtained by concentration under reduced pressure
  2. extractionwas extracted with ethyl acetate
  3. washwashed with water, twice with saturated aqueous sodium hydrogen carbonate solution, and aqueous sodium chloride solution
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1c66c55cd3054a8987ea98100c12c731
Source dataset
uspto-grants-2013_07
Patent number
US08481537B2

Linked notes

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