Potassium Carbonate → (4-chloro-3-nitrophenoxy)acetic Acid Methyl Ester

HRID 1944294Notes

Reaction equation

HRID 1944294 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][C:20](=[O:23])[CH2:21]Br>CN(C)C=O>[CH3:18][O:19][C:20](=[O:23])[CH2:21][O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 691274-Chloro-3-nitrophenol

Product 1

HCID 66717584(4-chloro-3-nitrophenoxy)acetic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chloro-3-nitrophenol (25 g), N,N-dimethylformamide (200 mL), potassium carbonate (60 g) and bromoacetic acid methyl ester (15.5 mL) was stirred at room temperature for 2.5 hours. The mixture was partitioned between ethyl acetate and water, and the aqueous phase extracted with ethyl acetate. The combined extracts were dried over sodium sulfate and then concentrated under reduced pressure. The residue was washed with diethyl ether to afford title compound as a white solid (30 g).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. extractionthe aqueous phase extracted with ethyl acetate
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-92dd6ffd4f50446a8beeba5e5cf8654c
Source dataset
uspto-grants-2013_03
Patent number
US08394830B2

Reaction notes

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