Sulfuric Acid → 1-bromo-3-ethyl-5-nitroBenzene

HRID 1452050

Reaction equation

HRID 1452050 reaction equation
[CH2:1]([C:3]1[CH:9]=[C:8]([Br:10])[C:6](N)=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1)[CH3:2].S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(O)C>[Br:10][C:8]1[CH:6]=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=[C:3]([CH2:1][CH3:2])[CH:9]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 199734682-Bromo-4-ethyl-6-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 189298701-bromo-3-ethyl-5-nitroBenzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 4-ethyl-2-nitro-6-bromoaniline (6.62g, 27mmol) in ethanol (40mL). Add, by dropwise addition, concentrated sulfuric acid (5mL) and heat at reflux, adding sodium nitrite (4.55g, mmol) in small portions over 25 minutes. Stir at room temperature for several hours, pour onto ice and extract into ethyl acetate. Wash with water (3×) and brine (3×). Dry (MgSO4) and evaporate the solvent in vacuo and purify by silica gel chromatography to give 3-bromo-5-ethylnitrobenzene.

Workup

  1. temperatureheat
  2. temperatureat reflux
  3. additionpour onto ice
  4. extractionextract into ethyl acetate
  5. washWash with water (3×) and brine (3×)
  6. dry with materialDry (MgSO4)
  7. customevaporate the solvent in vacuo
  8. custompurify by silica gel chromatography

Sources & evidence

ORD record
ord-3537f4ef0a8b4604818f49ac23273f0b
Source dataset
uspto-grants-1997_02
Patent number
US05606063

Linked notes

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