Potassium Carbonate → 3,4-Difluoro-5-(4-pentylphenyl)toluene

HRID 2260918Notes

Reaction equation

HRID 2260918 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[C:8]1[CH:9]=[C:10]([CH3:16])[CH:11]=[C:12]([F:15])[C:13]=1[F:14].[CH2:17]([C:22]1[CH:27]=[CH:26][C:25](OB(O)O)=[CH:24][CH:23]=1)[CH2:18][CH2:19][CH2:20][CH3:21]>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].C1(C)C=CC=CC=1.[Pd]>[F:15][C:12]1[CH:11]=[C:10]([CH3:16])[CH:9]=[C:8]([C:25]2[CH:24]=[CH:23][C:22]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:27][CH:26]=2)[C:13]=1[F:14]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 231188351,2-Difluoro-3-iodo-5-methylbenzeneHCID 234509174-Pentylphenylboric acid

Product 1

HCID 231188243,4-Difluoro-5-(4-pentylphenyl)tolueneYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

5.74 g of TBAB, 9.84 g of potassium carbonate and 0.76 g of Pd/C were added to 9.04 g of the compound (21) having been dissolved in a mixed solvent of 50 mL of toluene and 50 mL of Solmix, and 6.84 g of 4-pentylphenylboric acid, followed by stirring under refluxing by heating for 4 hours. After removing Pd/C by filtration, the filtrate was separated, and the aqueous layer as extracted with toluene, which was added to the organic layer. The organic layer was washed with a saturated potassium hydrogensulfite aqueous solution and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain 8.93 g of 3,4-difluoro-5-(4-pentylphenyl)toluene (22).

Workup

  1. temperatureunder refluxing
  2. temperatureby heating for 4 hours
  3. customAfter removing Pd/C
  4. filtrationby filtration
  5. customthe filtrate was separated
  6. extractionthe aqueous layer as extracted with toluene, which
  7. additionwas added to the organic layer
  8. washThe organic layer was washed with a saturated potassium hydrogensulfite aqueous solution and saturated saline
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off
  11. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-11f61efa21b342c2a3e12ce7be841101
Source dataset
uspto-grants-2010_12
Patent number
US07846513B2

Reaction notes

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