1,2-Dibromoethane → HCID 20735779, compound

HRID 1494498Notes

Reaction equation

HRID 1494498 reaction equation
BrCCBr.Cl[C:6]1([F:24])[C:11](Cl)([F:12])[O:10][C:9]([F:18])([C:14]([F:17])([F:16])[F:15])[C:8]([F:23])([C:19]([F:22])([F:21])[F:20])[O:7]1>[Zn].CN(C=O)C>[F:18][C:9]1([C:14]([F:15])([F:16])[F:17])[C:8]([F:23])([C:19]([F:22])([F:21])[F:20])[O:7][C:6]([F:24])=[C:11]([F:12])[O:10]1

Participants

5

Reactant 2

HCID 78391,2-DibromoethaneHCID 19828280HCID 19828280, compound2×

Product 1

HCID 20735779HCID 20735779, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 16.4 g (0.25 mol) of zinc dust, 200 mL of dry DMF, and 2 mL of 1,2-dibromoethane was stirred under N2 while a small portion of 41 g (0.112 mol) of 20 was added. The mixture was heated until reaction had started (ca. 90° C.), then the remainder of 20 was added dropwise at a rate sufficient to maintain temperature up to 105° C. in the pot while product was taken overhead as formed, bp 60°-65° C. When the addition had been completed, the pot temperature was increased until distillate was being collected at 135° C. The distillate was washed with water, dried over CaSO4, filtered and distilled to afford 14.2 g (43%) of perfluoro-2,3-dimethyl-2,3-dihydro-1,4-dioxin (21), bp 65°-67.5° C.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated until reaction
  3. custom(ca. 90° C.)
  4. customas formed
  5. additionWhen the addition
  6. temperaturethe pot temperature was increased until distillate
  7. customwas being collected at 135° C
  8. washThe distillate was washed with water
  9. dry with materialdried over CaSO4
  10. filtrationfiltered
  11. distillationdistilled

Sources & evidence

ORD record
ord-f8ef1f150dc74f969643bdcc34a87820
Source dataset
uspto-grants-1991_06
Patent number
US05026801

Reaction notes

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