1,4-Difluorobenzene → HCID 68572679, compound

HRID 747638Notes

Reaction equation

HRID 747638 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.C([Li])CCC.[N+:14]([C:17]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:18]=1[CH:19]=[O:20])([O-:16])=[O:15].[Cl-].[NH4+]>O1CCCC1>[N+:14]([C:17]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:18]=1[CH:19]([C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[F:8])[OH:20])([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 108921,4-DifluorobenzeneHCID 25517Ammonium ChlorideHCID 811235-Chloro-2-nitrobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 68572679HCID 68572679, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 15 g of 2,5-difluorobenzene dissolved in 150 ml of tetrahydrofuran are added, at −70° C., 50 ml of 1.6M butyllithium solution. After 2 hours at −70° C., 9.616 g of 2-nitro-5-chlorobenzaldehyde are introduced and the mixture is left at this temperature for 3 hours and then at room temperature for 18 hours. The medium is hydrolysed with ammonium chloride solution and extracted with ethyl acetate. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is filtered through silica, eluting with dichloromethane, to give 8.89 g of the expected product.

Workup

  1. additionare added, at −70° C.
  2. waitthe mixture is left at this temperature for 3 hours
  3. waitat room temperature for 18 hours
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. filtrationThe residue is filtered through silica
  8. washeluting with dichloromethane

Sources & evidence

ORD record
ord-1126bd82806d4506b42256b5d58b37b0
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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