Guaiacol → N-[2-fluoro-5-(2-methoxyphenoxy)-4-nitrophenyl]acetamide

HRID 433717Notes

Reaction equation

HRID 433717 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[F:21][C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[C:25](F)=[CH:24][C:23]=1[NH:32][C:33](=[O:35])[CH3:34]>O>[F:21][C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[C:25]([O:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])=[CH:24][C:23]=1[NH:32][C:33](=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 460GuaiacolHCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 14624893N-(2,5-Difluoro-4-nitrophenyl)acetamide

Product 1

HCID 21933575N-[2-fluoro-5-(2-methoxyphenoxy)-4-nitrophenyl]acetamideYield 86.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.73 g of 2-methoxyphenol and 5.5 g of potassium carbonate were added to 20 ml of N,N-dimethylformamide, and the mixture was heated to 60%. Into this mixture was added dropwise a solution comprising 4.3 g of N-(2,5-difluoro-4-nitrophenyl)acetamide and 30 ml of N,N-dimethylformamide at temperature from 60 to 65° C. The temperature of the mixture was kept for 1 hour while stirring, then, the mixture was cooled to room temperature, 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 to obtain 5.52 g of N-[2-fluoro-5-(2-methoxyphenoxy)-4-nitrophenyl]acetamide.

Workup

  1. temperaturethe mixture was heated to 60%
  2. additionInto this mixture was added dropwise a solution
  3. customfrom 60 to 65° C
  4. extractionextracted with ethyl acetate
  5. washthe organic layer was washed with dilute hydrochloric acid
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bc73d05eb51f4727bd09c0d47c628a44
Source dataset
uspto-grants-2003_12
Patent number
US06667413B2

Reaction notes

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