Potassium Nitrate → 2,5-Difluoro-1-methyl-3-nitrobenzene

HRID 1857418Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH3:9].[N+:10]([O-])([O-:12])=[O:11].[K+]>OS(O)(=O)=O>[F:1][C:2]1[C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH3:9]

Participants

Conditions

Temperature: 28 °C

Procedure

To a stirred solution of 2,5-difluorotoluene (0.544 g, 4.25 mmol, Aldrich, used as received) in conc. H2SO4 (5.0 mL) at 0° C., KNO3 (0.430 g, 4.25 mmol) was added in one portion. The resulting pale yellow solution was warmed to 28° C. and stirred at that temperature overnight. It was then poured into ice (25 g) and extracted with ethyl acetate (40 mL). The extract was dried over Na2SO4 and evaporated to afford 0.555 g (91%) of the title compound as a light red oil; 1H NMR (CDCl3): 2.369 (d, 3H, J=1.8 Hz), 7.127 (dd, 1H, J1 =8.1 Hz, J2 =6.0 Hz), 7.734 (dd, 1H, J1 =8.4 Hz, J2 =6.3 Hz).

Workup

extractionextracted with ethyl acetate (40 mL)
dry with materialThe extract was dried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-7a81ac6fc04949d2aa53239f919dfa9e
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06147075

Reaction notes

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