Guaiacol → HCID 10979585, compound

HRID 1585228Notes

Reaction equation

HRID 1585228 reaction equation
[C:1]1([O:8][CH3:9])[C:2](=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:3].[Br:10][C:11]([F:17])([F:16])[C:12]([F:15])([F:14])Br.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Br:10][C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[O:3][C:2]1[CH:4]=[CH:5][CH:6]=[CH:7][C:1]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 11430Potassium CarbonateHCID 313011,2-Dibromo-1,1,2,2-tetrafluoroethane

Product 1

HCID 10979585HCID 10979585, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

30.0 g of guaiacol, 70.0 g of 1,2-dibromotetrafluoroethane, 50.0 g of anhydrous potassium carbonate and 450 ml of dry DMSO were introduced into a stirred autoclave made of stainless steel. After the autoclave had been flushed with argon, it was sealed and subsequently heated to 100° C. After the reaction mixture had been stirred at this temperature for 24 hours, it was cooled to 20° C., poured into water and extracted with dichloromethane. The combined extracts were dried over magnesium sulfate. The dichloromethane was then evaporated in vacuo and the residue was distilled. 62.3 g of a mixture of 70 area % of 1-(2-bromo-1,1,2,2-tetrafluoroethoxy)-2-methoxybenzene (59.2% of theory) and 30 area % of 1-(1,1,2,2-tetrafluoroethoxy)-2-methoxybenzene (GC analysis) were obtained, distilling over at 80-95° C./14 mbar.

Workup

  1. customAfter the autoclave had been flushed with argon, it
  2. customwas sealed
  3. temperatureit was cooled to 20° C.
  4. additionpoured into water
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined extracts were dried over magnesium sulfate
  7. customThe dichloromethane was then evaporated in vacuo
  8. distillationthe residue was distilled

Sources & evidence

ORD record
ord-e1820b5c08af4caba1f557ace23f1ad2
Source dataset
uspto-grants-1999_08
Patent number
US05936102

Reaction notes

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