Nitric Acid → 2-(2-Chloro-4-fluoro-5-nitrophenyl)acetic acid

HRID 1257180Notes

Reaction equation

HRID 1257180 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[CH2:13][C:14]([OH:16])=[O:15]>OS(O)(=O)=O>[Cl:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([N+:1]([O-:4])=[O:2])=[CH:8][C:7]=1[CH2:13][C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 27250612-(2-Chloro-4-fluorophenyl)acetic acid

Product 1

HCID 689833332-(2-Chloro-4-fluoro-5-nitrophenyl)acetic acidYield 98%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

HNO3 (10.35 g, 98.6 mmol) was added drop-wise to a −10° C. solution of 2-(2-chloro-4-fluorophenyl)acetic acid (16.9 g, 89.6 mmol) in conc. H2SO4 (60 mL), stirred at 0° C. for 10 min, then carefully poured into ice water. The off-white solid was collected by filtration and dried to give 2-(2-chloro-4-fluoro-5-nitrophenyl)acetic acid (20.5 g, 98% yield). 1H NMR (400 Hz, DMSO-d6): δ 12.71 (br s, 1H), 8.33 (d, J=8.0 Hz, 1H), 7.92 (d, J=11.2 Hz, 1H), 3.85 (s, 2H).

Workup

  1. filtrationThe off-white solid was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-782fc78276324bcd8e419297c4e6bb13
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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