1,2-Difluorobenzene → HCID 21477972, compound

HRID 2374117Notes

Reaction equation

HRID 2374117 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13].[CH:14](=[O:23])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[Cl-].[NH4+]>C1COCC1>[F:6][C:7]1[C:8]([F:13])=[CH:9][CH:10]=[CH:11][C:12]=1[CH:14]([OH:23])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 97061,2-DifluorobenzeneHCID 25517Ammonium ChlorideHCID 31289NonanalHCID 178418339Butyllithium

Product 1

HCID 21477972HCID 21477972, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Butyllithium (2.5 M in hexanes 52.5 ml, 0.131 mol) was added dropwise to a stirred, cooled (−78° C.) solution of difluorobenzene (12.0 g, 0.105 mol) in dry THF (400 ml) under a stream of dry nitrogen. The reaction mixture was maintained under these conditions for 2.5 h and a solution of nonanal (14.9 g, 0.105 mol) in dry THF (50 ml) was added dropwise at −78° C. The mixture was allowed to slowly reach room temperature overnight. Ammonium chloride solution (2M, 200 ml) was added and the product was extracted into ether (2×150 ml), the combined ethereal extracts were washed with water and dried (MgSO4). The solvent was removed in vacuo and the residue was distilled under reduced pressure to give a colourless oil.

Workup

  1. temperatureThe reaction mixture was maintained under these conditions for 2.5 h
  2. customwas allowed to slowly reach room temperature overnight
  3. extractionthe product was extracted into ether (2×150 ml)
  4. washthe combined ethereal extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. distillationthe residue was distilled under reduced pressure
  8. customto give a colourless oil

Sources & evidence

ORD record
ord-bea9daa0aa9c4e17911f833deb936290
Source dataset
uspto-grants-2008_12
Patent number
US07462427B2

Reaction notes

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