Water → 4-Bromo-2-(tert-butoxy)-1-nitrobenzene

HRID 1528053Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[CH3:12][C:13]([CH3:16])([O-:15])[CH3:14].[K+].O>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:15][C:13]([CH3:16])([CH3:14])[CH3:12])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-bromo-2-fluoro-1-nitrobenzene (25.2 g) in THF (250 mL) was added potassium tert-butoxide (25.3 g) portionwise at 0° C., and the mixture was stirred at 0° C. for 30 min. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (28.6 g).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-31f36e263b34459583e249681069b85f
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090586B2

Reaction notes

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