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

HRID 2214383Notes

Reaction equation

HRID 2214383 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-dfbf25ad4f8c44979986d7b75377df3e
Source dataset
uspto-grants-2006_09
Patent number
US07109148B2

Reaction notes

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