Hydrochloric Acid → 2-(2-Chloro-4-fluoro-5-methoxycarbonylaminophenoxy)phenol

HRID 1280386Notes

Reaction equation

HRID 1280386 reaction equation
[Cl:1][C:2]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])=[CH:7][C:5]([NH2:6])=[C:4]([F:17])[CH:3]=1.Cl[C:19]([O:21][CH3:22])=[O:20].CN(C)C1C=CC=CC=1.Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([F:17])[C:5]([NH:6][C:19]([O:21][CH3:22])=[O:20])=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 6586Methyl chloroformateHCID 187592804-Chloro-2-fluoro-5-(2-hydroxyphenoxy)aniline

Product 1

HCID 187593032-(2-Chloro-4-fluoro-5-methoxycarbonylaminophenoxy)phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a mixture of 4-chloro-2-fluoro-5-(2-hydroxyphenoxy)aniline [Intermediate Compound A3-4], methyl chloroformate and tetrahydrofuran is added dropwise N,N-dimethylaniline, and the mixture is stirred at room temperature. Dilute hydrochloric acid is added to the reaction solution, and this is extracted with ethyl acetate. The organic layer is washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated to obtain 2-(2-chloro-4-fluoro-5-methoxycarbonylaminophenoxy)phenol [Intermediate compound A9-4].

Workup

  1. extractionthis is extracted with ethyl acetate
  2. washThe organic layer is washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-10b0a544bbfa44efb777ba4daee6d585
Source dataset
uspto-grants-2002_09
Patent number
US06451740B2

Reaction notes

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