Nitric Acid → 1-Bromo-4-fluoro-2-methyl-5-nitrobenzene

HRID 522705

Reaction equation

HRID 522705 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH3:9].[N+:10]([O-])([OH:12])=[O:11]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]([F:8])=[CH:4][C:3]=1[CH3:9]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 967432-Bromo-5-fluorotoluene

Product 1

HCID 100369831-Bromo-4-fluoro-2-methyl-5-nitrobenzeneYield 104.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Combine 1-bromo-4-fluoro-2-methylbenzene (30.0 g, 159 mmol) in concentrated sulfuric acid (100 mL), cool to about −5° C., and treat dropwise with nitric acid (11.00 mL, 174 mmol) over 20 minutes. Allow reaction mixture to warm to RT and stir for 30 min. Pour onto crushed ice with stirring and partition with tert-butyl methyl ether (MTBE) (200 mL). Separate the aqueous layer and extract with MTBE (2×50 mL). Combine organic layers, dry and concentrate under reduced pressure to provide 1-bromo-4-fluoro-2-methyl-5-nitrobenzene as an orange-colored viscous oil (39.0 g).

Workup

  1. customAllow reaction mixture
  2. additionPour
  3. customonto crushed ice
  4. stirringwith stirring
  5. custompartition with tert-butyl methyl ether (MTBE) (200 mL)
  6. customSeparate the aqueous layer
  7. extractionextract with MTBE (2×50 mL)
  8. customCombine organic layers, dry
  9. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-10aeb7632329498392241d80648555f9
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Linked notes

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