Nitric Acid → N-[4-fluoro-2-nitro-6-(trifluoromethyl)phenyl]acetamide

HRID 54364Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To 2-acetamido-5-fluorobenzotrifluoride (1.369 g, 6.19 mmol) in concentrated H2SO4 (6 mL) at 0° C. was added dropwise 70% HNO3 (0.8 mL, Baker). The mixture was stirred at 0° C. for 0.5 h, then at room temperature for 3 h and it was poured into ice water (25 g). The precipitate was collected by filtration, affording 2.1 g of crude 2-acetamido-5-fluoro-3-nitrobenzotrifluoride. It was crystallized from EtOH/H2O to afford 1.50 g of pure compound as yellow needles.

Workup

waitat room temperature for 3 h
filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record: ord-e3ea6d41cd944af5b399fa1e23324e63
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05622952

Reaction notes

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