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

HRID 1280365Notes

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

Conditions

Temperature: 60 °C

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° C. 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

additionInto this mixture was added dropwise a solution
customfrom 60 to 65° C
temperaturethe mixture was cooled to room temperature
extractionextracted with ethyl acetate
washthe organic layer was washed with dilute hydrochloric acid
washwashed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-aacf2893846f44e5bebc01017d553abe
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451740B2

Reaction notes

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