Nitric Acid → 1-Chloro-4,5-difluoro-2-nitrobenzene

HRID 2241382Notes

Reaction equation

HRID 2241382 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([F:9])[CH:3]=1.[N+:10]([O-])([OH:12])=[O:11]>>[Cl:1][C:2]1[CH:3]=[C:4]([F:9])[C:5]([F:8])=[CH:6][C:7]=1[N+:10]([O-:12])=[O:11]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 1365194-Chloro-1,2-difluorobenzene

Product 1

HCID 101303301-Chloro-4,5-difluoro-2-nitrobenzeneYield 86%

Procedure

To 4-chloro-1,2-difluorobenzene (25.0 g, 168.3 mmol) cooled to 0° C. was added fuming nitric acid (50.0 ml, 168.3 mmol) dropwise over 30 minutes. The solution was warmed to room temperature and stirred for 2 hours. The solution was poured slowly over ice and the resultant mixture extracted with diethyl ether. The diethyl ether layers were washed with brine, dried with Na2SO4, filtered and concentrated to afford the product (28 g, 81% yield) as orange oil. 1H NMR (CDCl3, 400 MHz) δ 7.89 (s, 1H), 7.46 (s, 1H).

Workup

  1. additionThe solution was poured slowly over ice
  2. extractionthe resultant mixture extracted with diethyl ether
  3. washThe diethyl ether layers were washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bc3fcb7f8e0348aab994a3ea5fbf78b9
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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