Nitric Acid → 2-(4-Fluoro-2-methyl-5-nitrophenyl)acetic acid

HRID 1257177Notes

Reaction equation

HRID 1257177 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[C:8]([CH3:16])[CH:7]=1>>[F:5][C:6]1[C:11]([N+:1]([O-:4])=[O:2])=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[C:8]([CH3:16])[CH:7]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 50169502-(4-Fluoro-2-methylphenyl)acetic acid

Product 1

HCID 690381782-(4-Fluoro-2-methyl-5-nitrophenyl)acetic acidYield 97%

Conditions

Temperature
5 °C

Procedure

To stirring fuming HNO3 (90 wt %, 30.0 mL, 643 mmol) at −15° C. was added 4-fluoro-2-methylphenylacetic acid (15 g, 89.2 mmol) in portions such that the internal temperature remained below −10° C. After completing the addition the reaction was stirred with warming to 5° C. over 15 min. The mixture was poured onto ice (400 g), stirred vigorously until the ice had completely melted and the resulting solid was collected by filtration, rinsed well with H2O and dried on the filter to afford 2-(4-fluoro-2-methyl-5-nitrophenyl)acetic acid (18.43 g, 97% yield) as a pale yellow solid. 1H NMR (400 MHz, acetone-d6): δ 8.06 (d, J=7.6 Hz, 1H), 7.36 (d, J=12.0 Hz, 1H), 3.84 (s, 2H), 2.44 (s, 3H).

Workup

  1. customremained below −10° C
  2. additionthe addition the reaction
  3. additionThe mixture was poured onto ice (400 g)
  4. filtrationthe resulting solid was collected by filtration
  5. washrinsed well with H2O
  6. customdried on the
  7. filtrationfilter

Sources & evidence

ORD record
ord-b9c544c756d5403c94c0a904abb14164
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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