Water → HCID 69184975, compound

HRID 2174165Notes

Reaction equation

HRID 2174165 reaction equation
[F:1][C:2]1[CH:3]=[C:4](O)[CH:5]=[C:6]([F:8])[CH:7]=1.[C:10](=[O:13])([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]CCC.O.[CH3:26][CH2:27]C(C)=O>CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[F:8][CH:6]([CH2:7][CH:2]([F:1])[CH2:3][CH2:26][CH3:27])[CH2:5][CH2:4][O:13][C:10]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6569Methyl Ethyl Ketone2×HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 759283,5-Difluorophenol

Product 1

HCID 69184975HCID 69184975, compound

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

To 15.0 g of 3,5-difluorophenol (17) dissolved in 100 mL of MEK there were added 17.5 g of potassium carbonate, 4.09 g of TBAB and 24.5 g of bromooctane dissolved in 50 mL of MEK, with heating under reflux for 4 hours. After cooling and addition of water, the organic layer was separated and the aqueous layer was extracted with diethyl ether. The organic layers were combined, were washed with saturated brine, and were then dried over anhydrous magnesium sulfate. After evaporating the solvent there were obtained 27.9 g (115 mmol) of 3,5-difluorooctyloxybenzene (18).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted with diethyl ether
  6. washwere washed with saturated brine
  7. dry with materialwere then dried over anhydrous magnesium sulfate
  8. customAfter evaporating the solvent there

Sources & evidence

ORD record
ord-3e136b8e60284e94a8c7368765ed42e5
Source dataset
uspto-grants-2015_06
Patent number
US09059410B2

Reaction notes

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