2-Acetamido-5-bromo-3-nitrobenzotrifluoride → 4-Bromo-2-nitro-6-(trifluoromethyl)aniline

HRID 53771Notes

Reaction equation

HRID 53771 reaction equation
C([NH:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([Br:14])=[CH:7][C:6]=1[C:15]([F:18])([F:17])[F:16])(=O)C>Cl>[NH2:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([Br:14])=[CH:7][C:6]=1[C:15]([F:18])([F:16])[F:17]

Participants

3

Reactant 1

HCID 106876142-Acetamido-5-bromo-3-nitrobenzotrifluoride

Product 1

HCID 108506724-Bromo-2-nitro-6-(trifluoromethyl)anilineYield 75.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 2-acetamido-5-bromo-3-nitrobenzotrifluoride (400 mg, 1.258 mmol) in concentrated HCl (3.5 mL) was refluxed overnight, then it was extracted by ethyl acetate (2×3 mL). The extract was dried over Mg2SO4 and evaporated to give 261 mg (75.6%) of 2-amino-5-bromo-3-nitrobenzotrifluoride. 1H NMR (CDCl3): δ 6.663 (S, 2H); 7.825 (d, 1H, J=1.2 Hz); 8.487 (d, 1H, J=1.2 Hz).

Workup

  1. temperaturewas refluxed overnight
  2. extractionit was extracted by ethyl acetate (2×3 mL)
  3. dry with materialThe extract was dried over Mg2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-8e1898e2ab634e0f903a8dbc58161bd7
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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