Nitric Acid → Acetic acid 2,6-difluoro-3-nitrobenzyl ester

HRID 243249Notes

Reaction equation

HRID 243249 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[CH2:4][O:5][C:6](=[O:8])[CH3:7].[N+:14]([O-])([OH:16])=[O:15]>>[F:1][C:2]1[C:12]([N+:14]([O-:16])=[O:15])=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[CH2:4][O:5][C:6](=[O:8])[CH3:7]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 12084134Acetic acid 2,6-difluorobenzyl ester

Product 1

HCID 68157040Acetic acid 2,6-difluoro-3-nitrobenzyl esterYield 87%

Conditions

Temperature
0 °C

Procedure

Acetic acid 2,6-difluorobenzyl ester (8 g, 42.9 mmol) was added dropwise to fuming nitric acid (50 mL) at 0° C. and the reaction mixture stirred at 0° C. for 30 min. The reaction mixture was poured onto ice and the product extracted with DCM (3×30 mL). The combined organic fractions were washed with sat, aq, NaHCO3 then brine, dried (MgSO4) and concentrated in vacuo to give the title compound as a yellow oil (8.69 g, 87%). 1H NMR 300 MHz δ (CDCl3): 8.21-8.12 (1H, m), 7.09 (1H, ddd, J=9.6, 7.9, 1.9 Hz), 5.24 (2H, t, J=1.5 Hz), 2.10 (3H, s).

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionthe product extracted with DCM (3×30 mL)
  3. washThe combined organic fractions were washed
  4. dry with materialaq, NaHCO3 then brine, dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-49aecf2b84f348ada5c62ad46244ffaf
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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