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

HRID 2214380Notes

Reaction equation

HRID 2214380 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

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

Workup

  1. additionwas added
  2. stirringAfter stirring at the same temperature for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with diluted hydrochloric acid and water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. washThe resulting crystals were washed with t-butyl methyl ether

Sources & evidence

ORD record
ord-bbcee5241cf441f4b9449677a19a75fc
Source dataset
uspto-grants-2006_09
Patent number
US07109148B2

Reaction notes

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