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

HRID 1241290Notes

Reaction equation

HRID 1241290 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-199c93692124467e9ed697c74c3a2caa
Source dataset
uspto-grants-2006_10
Patent number
US07115544B2

Reaction notes

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