Nitric Acid → 2-(4-Bromo-3-nitro-phenyl)-3-(trifluoromethyl)-pyridine

HRID 968574Notes

Reaction equation

HRID 968574 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[N+:18]([O-])([OH:20])=[O:19]>OS(O)(=O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]([C:14]([F:17])([F:15])[F:16])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:6][C:7]=1[N+:18]([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 220302682-(4-Bromophenyl)-3-(trifluoromethyl)-pyridine

Product 1

HCID 220301962-(4-Bromo-3-nitro-phenyl)-3-(trifluoromethyl)-pyridine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 2-(4-bromophenyl)-3-(trifluoromethyl)-pyridine (0.93 mmol) in H2SO4 (4 mL) cautiously add fuming HNO3 (2 ml). Stir the mixture 30 minutes at room temperature. Pour the mixture onto ice-water (20 mL) and collect the precipitate. Dissolve the precipitate in EtOAc and neutralize with saturated NaHCO3, dry over Na2SO4, concentrate under vacuum to obtain 2-(4-bromo-3-nitro-phenyl)-3-(trifluoromethyl)-pyridine.

Workup

  1. additionPour the mixture onto ice-water (20 mL)
  2. customcollect the precipitate
  3. dissolutionDissolve the precipitate in EtOAc
  4. dry with materialdry over Na2SO4
  5. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-2bc307dcdc2f4e9998b1c6deb272b3fc
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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