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

HRID 1280370Notes

Reaction equation

HRID 1280370 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

Into 10 ml of boron trifluoride methanol complex, methanol solution was added 0.25 g of methyl [2-(5-acetylamino-2-chloro-4-fluorophenoxy)phenoxy]acetate, and the mixture was heated for 3 hours while stirring. Thereafter, the reaction solution was concentrated, the residue was dissolved in ethyl acetate, and washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated to obtain 0.2 g of methyl [2-(5-amino-2-chloro-4-fluorophenoxy)phenoxy]acetate [Intermediate compound A3-22].

Workup

  1. temperaturethe mixture was heated for 3 hours
  2. concentrationThereafter, the reaction solution was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a93d03fb060f46de92d567679093ea49
Source dataset
uspto-grants-2002_09
Patent number
US06451740B2

Reaction notes

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