Nitric Acid → 1,3-Dibromo-5-fluoro-2-methoxy-4-nitrobenzene

HRID 1404085Notes

Reaction equation

HRID 1404085 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Br:9])[C:3]=1[O:10][CH3:11].[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:12]([O-:14])=[O:13])=[C:4]([Br:9])[C:3]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 27739651,3-Dibromo-5-fluoro-2-methoxybenzene

Product 1

HCID 225046691,3-Dibromo-5-fluoro-2-methoxy-4-nitrobenzeneYield 73.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

The solution of 8-3 (273.4 g, 0.963 mol) dissolved in concentrated H2SO4 (1.6 L) at 0° C. The mixture of conc.HNO3 (63.2 mL) and conc. H2SO4 (400 mL) was added dropwise over 1 h. The color of the reaction became orange. TLC monitored the starting material was disappeared. The reaction mixture was poured onto crushed ice and extracted with ethyl acetate (800 mL×3). The combined organic layers were combined and were concentrated in vacuo to 400 mL, which was cooled under ice bath to afforded 8-4 (234.2 g, 73.9%) as a white solid.

Workup

  1. additionThe mixture of conc
  2. additionThe reaction mixture was poured
  3. customonto crushed ice
  4. extractionextracted with ethyl acetate (800 mL×3)
  5. concentrationwere concentrated in vacuo to 400 mL, which
  6. temperaturewas cooled under ice bath

Sources & evidence

ORD record
ord-8ca461428a9345fdb17ba32066afb521
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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