Potassium Nitrate → 4-Bromo-2,5-difluoronitrobenzene

HRID 715506Notes

Reaction equation

HRID 715506 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[F:9].[N+:10]([O-])([O-:12])=[O:11].[K+]>OS(O)(=O)=O>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[F:9]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 678622-Bromo-1,4-difluorobenzene

Product 1

HCID 27362864-Bromo-2,5-difluoronitrobenzeneYield 78.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a stirred solution of 2-bromo-1,4-difluoro-benzene (98.6 g, 510.88 mmol) in 1.2 L of concentrated H2SO4 was added KNO3 by portions at 0° C. After this addition, the mixture was allowed to warm to RT and stirred for additional 16 h. The mixture was poured onto ice-cold water and extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give 1-bromo-2,5-difluoro-4-nitro-benzene (95 g, 78.1% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.91-7.87 (dd, 1H), 7.52-7.57 (dd, 1H).

Workup

  1. additionAfter this addition
  2. additionThe mixture was poured onto ice-cold water
  3. extractionextracted with DCM
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0e8b5049f5224b2b882f564b8d8eaec0
Source dataset
uspto-grants-2015_11
Patent number
US09187464B2

Reaction notes

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