Methyl [2-(5-acetylamino-2-chloro-4-fluorophenoxy)phenoxy]acetate → Methyl [2-(5-amino-2-chloro-4-fluorophenoxy)phenoxy]acetate

HRID 493940Notes

Reaction equation

HRID 493940 reaction equation
C([NH:4][C:5]1[C:6]([F:25])=[CH:7][C:8]([Cl:24])=[C:9]([CH:23]=1)[O:10][C:11]1[CH:22]=[CH:21][CH:20]=[CH:19][C:12]=1[O:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])(=O)C>CO>[NH2:4][C:5]1[C:6]([F:25])=[CH:7][C:8]([Cl:24])=[C:9]([CH:23]=1)[O:10][C:11]1[CH:22]=[CH:21][CH:20]=[CH:19][C:12]=1[O:13][CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

3

Reactant 1

HCID 21053881Methyl [2-(5-acetylamino-2-chloro-4-fluorophenoxy)phenoxy]acetate

Product 1

HCID 23380315Methyl [2-(5-amino-2-chloro-4-fluorophenoxy)phenoxy]acetateYield 90.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 10 ml of a methanol solution of a boron trifluoride methanol complex was added 0.25 g of methyl [2-(5-acetylamino-2-chloro-4-fluorophenoxy)phenoxy]acetate, and the mixture was heated and stirred for 3 hours. The reaction mixture was then concentrated. The residue was dissolved in ethyl acetate, and the solution was washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, and then concentrated to give 0.2 g of methyl [2-(5-amino-2-chloro-4-fluorophenoxy)phenoxy]acetate.

Workup

  1. temperaturethe mixture was heated
  2. concentrationThe reaction mixture was then concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6ffb9b85016a43518f3e11747afc604f
Source dataset
uspto-grants-2009_05
Patent number
US07538072B2

Reaction notes

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