Water → 4-Chloro-2-fluoro-5-isopropoxy-nitrobenzene

HRID 1981579Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].[CH:19](I)([CH3:21])[CH3:20].O>C(#N)C>[Cl:1][C:2]1[C:3]([O:12][CH:19]([CH3:21])[CH3:20])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([F:8])[CH:7]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 2-chloro-4-fluoro-5-nitrophenol (19.1 g) in acetonitrile (100 ml), there was added anhydrous potassium carbonate (8 g). After stirring at room temperature (ca. 20° C.) for several minutes, isopropyl iodide (25 g) was added thereto, and the resultant mixture was heated under reflux for 3 hours. After being allowed to cool to room temperature (ca. 20° C.), water was added thereto, and the reaction mixture was extracted with ether. The ether extract was washed with a 5% aqueous sodium hydroxide solution and water in order, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was recrystallized from ethanol to give 13.5 g of 4-chloro-2-fluoro-5-isopropoxynitrobenzene. M.P., 61.3°-62.4° C.

Workup

temperatureunder reflux for 3 hours
additionwas added
extractionthe reaction mixture was extracted with ether
extractionThe ether extract
washwas washed with a 5% aqueous sodium hydroxide solution and water in order
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was recrystallized from ethanol

Sources & evidence

ORD record: ord-40a3dbbc38dd419a9bbfc4f1b49410a3
Source dataset: uspto-grants-1986_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04593094

Reaction notes

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