Trifluoroacetic acid → 4-Bromo-3-methyl-5-nitroaniline

HRID 2216052Notes

Reaction equation

HRID 2216052 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([Br:17])=[C:10]([CH3:18])[CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[Br:17][C:11]1[C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:8]([NH2:7])=[CH:9][C:10]=1[CH3:18]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 69586631(4-Bromo-3-methyl-5-nitro-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 218864724-Bromo-3-methyl-5-nitroanilineYield 112.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Bromo-3-methyl-5-nitro-phenyl)-carbamic acid tert-butyl ester (1000 mg, 2.9 mmol) was dissolved into DCM (10 mL). To this was added TFA (10 mL) and the reaction was stirred at RT for 1 hour. The pH was adjusted to 8 with 1 N NaOH and the solvents were removed in vacuo. The reaction mixture was dissolved into EtOAc and the layers were separated. The organic layers were dried (MgSO4) and the solvents were removed in vacuo resulting in title compound (756 mg, quantitative) as a brown oil. 1H-NMR (CDCl3): δ 8.44 (s, 1H), 8.02 (s, 1H), 7.61 (s, 1H), 3.05 (s, 3H).

Workup

  1. customthe solvents were removed in vacuo
  2. dissolutionThe reaction mixture was dissolved into EtOAc
  3. customthe layers were separated
  4. dry with materialThe organic layers were dried (MgSO4)
  5. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-bbcb2cd734e446098911be32e8cbf4b8
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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