Nitric Acid → 2-Acetamido-5-bromo-3-nitrobenzotrifluoride

HRID 54358Notes

Reaction equation

HRID 54358 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([Br: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]([Br:11])=[CH:7][C:6]=1[C:12]([F:15])([F:13])[F:14])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 27734174'-Bromo-2'-(trifluoromethyl)acetanilide

Product 1

HCID 106876142-Acetamido-5-bromo-3-nitrobenzotrifluorideYield 90%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To 2-acetamido-5-bromobenzotrifluoride (665 mg, 2.436 mmol) in concentrated H2SO4 (4 mL) at 0° C. was added dropwise 70% HNO3 (0.4 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 (15 g). The precipitate was collected by filtration, affording 700 mg (90%) of crude 2-acetamido-5-bromo-3-nitrobenzotrifluoride. It was crystallized from EtOH/H2O to offer 610 mg (78.8%) of pure compound as white needles. Mp: 193°-5° C., 1H NMR (CDCl3): δ2.250 (s, 3H), 7.346 (s, 1H), 8.039 (s, 1H); 8.247 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-e3fe4276d2c24c81ac5c8c372880a5e1
Source dataset
uspto-grants-1997_04
Patent number
US05622952

Reaction notes

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