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

HRID 1831487Notes

Reaction equation

HRID 1831487 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 80%

Procedure

To a 1-chloro-3,4-difluorobenzene (25 g, 0.17 mol) cooled to 0° C. was added fuming nitric acid (50 mL) dropwise over 30 min. The orange solution was warmed to room temperature and stirred for 2 h. The solution was poured slowly over ice and the resultant mixture extracted with diethyl ether. The diethyl ether layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give 26 g (80%) of 1-chloro-4,5-difluoro-2-nitro-benzene: Crude 1H NMR (400 MHz, CDCl3): δ 7.88 (dd, J=9.3, 7.6 Hz, 1H), 7.43 (dd, J=9.3, 7.1 Hz, 1H). The crude material was pure enough to carry on to the next step.

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 (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17e4d2ac77ca415dab3e3d7e9e0669c8
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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