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

HRID 493935Notes

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

First, 2.73 g of 2-methoxyphenol and 5.5 g of potassium carbonate were added to 20 ml of N,N-dimethylformamide, and the temperature was increased to 60° C. To the mixture was added dropwise a solution consisting of 4.3 g of N-(2,5-difluoro-4-nitrophenyl)acetamide and 30 ml of N,N-dimethylformamide at a temperature of 60° C. to 65° C. After stirring while keeping the temperature for 1 hour, the mixture was cooled to room temperature and then 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 to give 5.52 g of N-[2-fluoro-5-(2-methoxyphenoxy)-4-nitrophenyl]acetamide.

Workup

additionTo the mixture was added dropwise a solution
customfor 1 hour
temperaturethe mixture was cooled to room temperature
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with diluted hydrochloric acid and water
dry with materialdried over magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-9d069d5261694b7f90b957e86a5df2cd
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538072B2

Reaction notes

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