Water → HCID 19980942, compound

HRID 2174163Notes

Reaction equation

HRID 2174163 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][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].O>CCC(C)=O.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[CH2:30]([O:11][C:3]1[C:2]([F:1])=[C:7]([F:8])[CH:6]=[C:5]([F:9])[C:4]=1[F:10])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19]

Participants

7

Reactant 4

HCID 962WaterHCID 89191-BromododecaneHCID 11430Potassium CarbonateHCID 698582,3,5,6-Tetrafluorophenol

Product 1

HCID 19980942HCID 19980942, 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 33.0 g of bromododecane 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 40.1 g (120 mmol) of 4-dodecyloxy-2,3,5,6-tetrafluorobenzene (12).

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-d764e55f4ee94e419756c3370b5e2855
Source dataset
uspto-grants-2015_06
Patent number
US09059410B2

Reaction notes

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