Water → HCID 22416124, compound

HRID 2174159Notes

Reaction equation

HRID 2174159 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O>CCC(C)=O.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[CH2:19]([O:11][C:3]1[C:2]([F:1])=[C:7]([F:8])[CH:6]=[C:5]([F:9])[C:4]=1[F:10])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 962WaterHCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 698582,3,5,6-Tetrafluorophenol

Product 1

HCID 22416124HCID 22416124, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

To 20.0 g of 2,3,5,6-tetrafluorophenol (1) dissolved in 100 mL of MEK there were added 18.3 g of potassium carbonate, 4.26 g of TBAB and 25.6 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. The solvent was evaporated to yield 33.4 g (120 mmol) of 4-octyloxy-2,3,5,6-tetrafluorobenzene (8).

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. customThe solvent was evaporated

Sources & evidence

ORD record
ord-0edc1b8626824123ac9bc6292468c661
Source dataset
uspto-grants-2015_06
Patent number
US09059410B2

Reaction notes

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