HCID 10400060, compound → HCID 10399121, compound

HRID 1293726Notes

Reaction equation

HRID 1293726 reaction equation
[CH2:1]([S:3][CH:4]([S:12][CH2:13][CH3:14])[C:5](F)([F:10])[C:6]([F:9])([F:8])[F:7])[CH3:2]>C(Cl)Cl.[OH-].[K+]>[CH2:13]([S:12][C:4]([S:3][CH2:1][CH3:2])=[C:5]([F:10])[C:6]([F:7])([F:8])[F:9])[CH3:14]

Participants

4

Reactant 1

HCID 10400060HCID 10400060, compound

Product 1

HCID 10399121HCID 10399121, compoundYield 125%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14797Potassium HydroxideSolvent

Procedure

A solution of 3,3-bis-ethylsulfanyl-1,1,1,2,2-pentafluoro-propane (example C.26 step 1) (125.8 g, 495 mmol) in DCM (495 mL) and 3M KOH (97.97 g KOH (85%) in 495 ML H2O), with a catalytic amount of n-BuN4Br (4.785 g, 3 mol %), was stirred at 23° C. for 3 h. The organic layer was separated and dried over MgSO4. The solvent was removed by cautious rotary evaporation (470 mbar, 40° C., 100 rpm) to give an orange liquid (ca. 145 g, 125%). Vacuum distillation gave the title compound as a colorless liquid (109.82 g, 95%; bp 86–87° C. at 32 mbar). [according to J. Org. Chem. 1993, 58(1), 29–31. MS (GC-MS; EI) 234.1 [(M)+].

Workup

  1. customwas stirred at 23° C. for 3 h
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed by cautious rotary evaporation (470 mbar, 40° C., 100 rpm)

Sources & evidence

ORD record
ord-f48e120487be48f8a7441476017e35e8
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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