Nitric Acid → Methyl 2,4-dinitro-5-fluorophenoxyacetate

HRID 2255178Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([CH:13]=1)[O:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].[N+:17]([O-])([OH:19])=[O:18].C(OCC)(=O)C.O>S(=O)(=O)(O)O>[N+:14]([C:5]1[CH:4]=[C:3]([N+:17]([O-:19])=[O:18])[C:2]([F:1])=[CH:13][C:6]=1[O:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])([O-:16])=[O:15]

Participants

Conditions

Temperature: 15 °C

Procedure

To a solution of 14.5 g (63 mmol) methyl 5-fluoro-2-nitrophenoxyacetate in 17 ml conc. sulfuric acid (H2SO4) at 8° C. was added slowly via an addition funnel a mixture of 5.0 ml (76 mmol) of 70% nitric acid and 5.0 ml of conc. H2SO4. After addition was complete, the reaction was stirred an additional 1 hour at 15° C. The reaction mixture was poured into 150 ml of 1:1 ethyl acetate/water and the resulting layers were separated. The aqueous phase was extracted with ethyl acetate (2×60 ml) and the combined organics were dried (Na2SO4) and concentrated in vacuo to give 17.2 g (98% yield) of the desired nitrated product as a yellow solid.

Workup

additionAfter addition
customthe resulting layers were separated
extractionThe aqueous phase was extracted with ethyl acetate (2×60 ml)
dry with materialthe combined organics were dried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d0ae2c96f58f47d2846b941833d6706b
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05238908

Reaction notes

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