Sodium sulfide nonahydrate → 4-(4,4-Difluoro-but-3-enyldisulfanyl)-1,1-difluoro-but-1-ene

HRID 650615

Reaction equation

HRID 650615 reaction equation
[S-:1][S-:2].[Na+].[Na+].O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].[S].Br[CH2:19][CH2:20][CH:21]=[C:22]([F:24])[F:23]>C(O)C>[F:23][C:22]([F:24])=[CH:21][CH2:20][CH2:19][S:1][S:2][CH2:19][CH2:20][CH:21]=[C:22]([F:24])[F:23]

Participants

6

Reactant 4

HCID 73972Sodium sulfide nonahydrateHCID 89870Sodium disulfideHCID 27822404-Bromo-1,1-difluorobut-1-eneHCID 5362487Sulfur

Product 1

HCID 217129114-(4,4-Difluoro-but-3-enyldisulfanyl)-1,1-difluoro-but-1-ene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of sodium disulfide (previously prepared from sodium sulfide nonahydrate (53 g) and sulfur (7.0 g) in ethanol (250 cm3)) was added to 1-bromo4,4-difluorobut-3-ene (50 g) in ethanol (100 cm3). The mixture was gradually heated and stirred under reflux for 2 hours, then cooled and evaporated under reduced pressure. The residue was extracted with diethyl ether, the organic phase filtered to remove sodium bromide and the ether evaporated under reduced pressure to give a liquid which was distilled at 16 mm Hg, bp 120° C. to give the bis-(4,4-difluorobut-3-enyl)disulfide (24 g) as a colourless liquid.

Workup

  1. temperatureThe mixture was gradually heated
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. customevaporated under reduced pressure
  5. extractionThe residue was extracted with diethyl ether
  6. filtrationthe organic phase filtered
  7. customto remove sodium bromide
  8. customthe ether evaporated under reduced pressure
  9. customto give a liquid which
  10. distillationwas distilled at 16 mm Hg, bp 120° C.

Sources & evidence

ORD record
ord-3475dfc603334e56b64100cc5912dc74
Source dataset
uspto-grants-2001_08
Patent number
US06274632B1

Linked notes

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