Water → Methyl [o-(5-fluoro-2-nitrophenoxy)phenoxy]acetate

HRID 21521

Reaction equation

HRID 21521 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[F:7][C:8]1[CH:9]=[CH:10][C:11]([N+:22]([O-:24])=[O:23])=[C:12]([CH:21]=1)[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:7][C:8]1[CH:9]=[CH:10][C:11]([N+:22]([O-:24])=[O:23])=[C:12]([CH:21]=1)[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH2:2][C:3]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 19932387o-(5-Fluoro-2-nitrophenoxy)phenol

Product 1

HCID 54233795Methyl [o-(5-fluoro-2-nitrophenoxy)phenoxy]acetateYield 81.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl bromoacetate (36.33 g, 0.24 mol) is added to a mixture of o-(5-fluoro-2-nitrophenoxy)phenol (39.45 g, 0.16 mol) and potassium carbonate (32.75 g, 0.24 mol) in N,N-dimethylformamide. The reaction mixture is stirred at room temperature for 18 hours, poured into water and extracted with ether. The organic extract is washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain the title product as a yellow solid (42 g) which is identified by 1HNMR spectral analysis.

Workup

  1. extractionextracted with ether
  2. extractionThe organic extract
  3. washis washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d2eaa8cd6bf449bc8dcd66174c984ef3
Source dataset
uspto-grants-1995_06
Patent number
US05424280

Linked notes

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