Nitric Acid → Benzene, 3-bromo-1-chloro-4-ethoxy-5-fluoro-2-nitro-

HRID 1404123Notes

Reaction equation

HRID 1404123 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([F:9])[C:3]=1[O:10][CH2:11][CH3:12].[N+:13]([O-])([OH:15])=[O:14]>OS(O)(=O)=O>[Br:1][C:2]1[C:7]([N+:13]([O-:15])=[O:14])=[C:6]([Cl:8])[CH:5]=[C:4]([F:9])[C:3]=1[O:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 58303959HCID 58303959, compound

Product 1

HCID 58304006Benzene, 3-bromo-1-chloro-4-ethoxy-5-fluoro-2-nitro-Yield 40%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 30-3 (48.6 g, 192 mmol) in concentrated H2SO4 (240 mL) stirred at room temperature was added HNO3 (19 mL) dropwise. The mixture was allowed to stir at room temperature for two hours. The reaction mixture was then poured into ice water and extracted with ethyl acetate (3×800 mL). The organic layer was combined and concentrated under vacuum to get a crude product which was purified on silica gel column chromatography eluting with petroleum ether/ethyl acetate (10:1 to 1:1) to afford 30-4 (22.9 g, 40%) as a yellow solid. LRMS: calc 296.9 and found: 297.9 [M+1].

Workup

  1. extractionextracted with ethyl acetate (3×800 mL)
  2. concentrationconcentrated under vacuum
  3. customto get a crude product which
  4. customwas purified on silica gel column chromatography
  5. washeluting with petroleum ether/ethyl acetate (10:1 to 1:1)

Sources & evidence

ORD record
ord-efb841e0f9b340e39afe1364f3b790ec
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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