Water → Methyl [2-(5-acetylamino-4-fluoro-2-nitrophenoxy)phenoxy]acetate

HRID 433719Notes

Reaction equation

HRID 433719 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[OH:18])=[CH:4][C:3]=1[NH:19][C:20](=[O:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]([O:33][CH3:34])=[O:32].O>CN(C)C=O>[C:20]([NH:19][C:3]1[C:2]([F:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[C:5]([CH:4]=1)[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:30][C:31]([O:33][CH3:34])=[O:32])(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 21933568N-[2-fluoro-5-(2-hydroxyphenoxy)-4-nitrophenyl]acetamide

Product 1

HCID 21053883Methyl [2-(5-acetylamino-4-fluoro-2-nitrophenoxy)phenoxy]acetateYield 80.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.02 g of N-[2-fluoro-5-(2-hydroxyphenoxy)-4-nitrophenyl]acetamide was dissolved in 20 ml of N,N-dimethylformamide, then, 1.5 g of potassium carbonate was added, and the mixture was stirred for 1 hour at room temperature. Then, 1.6 g of methyl bromoacetate was added at room temperature. The mixture was stirred for 2 hours under the same condition, poured into water, extracted with ethyl acetate, and the organic layer was washed with dilute hydrochloric acid, washed with water, dried over magnesium sulfate and concentrated, and the resulted crystal was washed with t-butyl methyl ether to obtain 3.01 g of methyl [2-(5-acetylamino-4-fluoro-2-nitrophenoxy)phenoxy]acetate.

Workup

  1. stirringThe mixture was stirred for 2 hours under the same condition
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with dilute hydrochloric acid
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. washthe resulted crystal was washed with t-butyl methyl ether

Sources & evidence

ORD record
ord-f477e60afbd441f8be5dc7c31a490802
Source dataset
uspto-grants-2003_12
Patent number
US06667413B2

Reaction notes

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