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

HRID 1930414Notes

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

Conditions

Temperature: 0 °C

Procedure

HNO3 (10.35 g, 98.6 mmol) was added dropwise to a stirred solution of 2-(2-chloro-4-fluorophenyl)acetic acid (16.9 g, 89.6 mmol) in conc. H2SO4 (60 mL) at −10° C. After complete addition, the resulting mixture was stirred at 0° C. for 10 min, and was 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, 98.2% yield). 1HNMR (400 Hz, DMSO-d6): δ 12.71 (br s, 1 H), 8.33 (d, J=8.0 Hz, 1 H), 7.92 (d, J=11.2 Hz, 1 H), 3.85 (s, 2 H).

Workup

additionAfter complete addition
filtrationThe off-white solid was collected by filtration
customdried

Sources & evidence

ORD record: ord-4a0bf7da0c4841728acc0481f1d44771
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

Loading…