Water → HCID 12084325, compound

HRID 1744748Notes

Reaction equation

HRID 1744748 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:16][C:17]1[CH:29]=[CH:28][C:27]2[C:26]3[C:21](=[C:22]([F:34])[C:23]([CH:30](O)[CH2:31][CH3:32])=[CH:24][CH:25]=3)[CH2:20][C:19]=2[C:18]=1[F:35])[CH2:13][CH2:14][CH3:15].O>S(=O)(=O)(O)O.C1(C)C=CC=CC=1>[CH2:12]([O:16][C:17]1[CH:29]=[CH:28][C:27]2[C:26]3[C:21](=[C:22]([F:34])[C:23]([CH2:30][CH2:31][CH3:32])=[CH:24][CH:25]=3)[CH2:20][C:19]=2[C:18]=1[F:35])[CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 22223131HCID 22223131, compound

Product 1

HCID 12084325HCID 12084325, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 1140TolueneSolvent

Procedure

After the addition of approx. 0.5 g of 4-toluenesulfonic acid and a few drops of concentrated sulfuric acid, a solution of 14 mmol of 2-butoxy-1,8-difluoro-7-(1-hydroxypropyl) fluorene in 50 ml of toluene is heated on a water separator for 3 h. After cooling, the mixture is extracted using 5 percent sodium hydrogencarbonate solution and saturated sodium chloride solution and dried over sodium sulfate. Then 0.5 g of palladium catalyst (10 percent on activated carbon) are subsequently added and the mixture is hydrogenated at room temperature. The reaction mixture is filtered and the solvent is removed under reduced pressure. The crude product is purified by chromatography on silica gel and recrystallization from heptane. 2-Butoxy-1,8-difluoro-7-n-propylfluorene is obtained.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture is extracted
  3. dry with materialdried over sodium sulfate
  4. additionThen 0.5 g of palladium catalyst (10 percent on activated carbon) are subsequently added
  5. customis hydrogenated at room temperature
  6. filtrationThe reaction mixture is filtered
  7. customthe solvent is removed under reduced pressure
  8. customThe crude product is purified by chromatography on silica gel and recrystallization from heptane

Sources & evidence

ORD record
ord-a622a469150145a3991b8be014b30798
Source dataset
uspto-grants-2006_03
Patent number
US07018685B2

Reaction notes

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