Water → Methyl [2-(2-chloro-4-fluoro-5-methoxycarbonylaminophenoxy)phenoxy]acetate

HRID 433738Notes

Reaction equation

HRID 433738 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([F:16])[C:13]([NH:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]([O:32][CH3:33])=[O:31].O>CN(C)C=O>[Cl:1][C:2]1[CH:15]=[C:14]([F:16])[C:13]([NH:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:29][C:30]([O:32][CH3:33])=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 187593032-(2-Chloro-4-fluoro-5-methoxycarbonylaminophenoxy)phenol

Product 1

HCID 86584265Methyl [2-(2-chloro-4-fluoro-5-methoxycarbonylaminophenoxy)phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(2-chloro-4-fluoro-5-methoxycarbonylaminophenoxy)phenol [Intermediate compound A9-4] is dissolved in N,N-dimethylformamide, then, potassium carbonate is added, and the mixture is stirred for 1 hour at room temperature. Then, methyl bromoacetate is added at room temperature. The mixture is stirred at 60° C. for 2 hours, poured into water, extracted with ethyl acetate, and the organic layer is washed with dilute hydrochloric acid and water, dried over magnesium sulfate and concentrated to obtain methyl [2-(2-chloro-4-fluoro-5-methoxycarbonylaminophenoxy)phenoxy]acetate [Intermediate compound A9-22].

Workup

  1. stirringThe mixture is stirred at 60° C. for 2 hours
  2. extractionextracted with ethyl acetate
  3. washthe organic layer is washed with dilute hydrochloric acid and water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a0ac829baf4442b2b840ea98884ca4d8
Source dataset
uspto-grants-2003_12
Patent number
US06667413B2

Reaction notes

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