Cesium fluoride → 7-Ethoxy-1,2-difluoronaphthalene

HRID 1873322Notes

Reaction equation

HRID 1873322 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([Si](C)(C)C)=[CH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([F:14])[C:10]([F:15])=[CH:9][CH:8]=2)[CH3:2].[F-].[Cs+]>CN(C=O)C.O>[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([F:15])=[C:11]2[F:14])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 25953Cesium fluorideHCID 58151894(3-Ethoxy-5,6-difluoronaphthalen-2-yl)trimethylsilane

Product 1

HCID 581519037-Ethoxy-1,2-difluoronaphthalene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

44.0 g (about 81.6 mmol) of (3-ethoxy-5,6-difluoronaphthalen-2-yl)trimethylsilane are stirred at 100° C. for 20 h together with 26.3 g (0.17 mol) of caesium fluoride in 300 ml of DMF. After cooling, the mixture is diluted with water and extracted a number of times with MTBE. The combined organic phases are washed with water and sat. sodium chloride soln., and the solution is dried using sodium sulfate. The brown oil remaining after removal of the solvent is purified by column chromatography (SiO2, toluene:ethyl acetate=9:1), giving 7-ethoxy-1,2-difluoronaphthalene as a brown oil.

Workup

  1. temperatureAfter cooling
  2. extractionextracted a number of times with MTBE
  3. washThe combined organic phases are washed with water and sat. sodium chloride soln
  4. custom, and the solution is dried
  5. customafter removal of the solvent
  6. customis purified by column chromatography (SiO2, toluene:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-a16c8f531d7241509eb7d13751ffc34a
Source dataset
uspto-grants-2012_11
Patent number
US08303844B2

Reaction notes

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