Dichloromethane → HCID 15766436, compound

HRID 861837Notes

Reaction equation

HRID 861837 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[CH2:16])[CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[H-].[Na+].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.C(Cl)Cl>CN(C=O)C.C(C1C=C(O)C=CC=1O)(C)(C)C>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([O:8][C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[CH2:16])[CH:10]=2)([C:4]([F:6])([F:5])[F:7])[C:2]([F:17])([F:18])[F:1])(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 73984-Chlorobenzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 15766435122056-08-0

Product 1

HCID 15766436HCID 15766436, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 16043Tert-ButylhydroquinoneCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

12 g (44.4 mmol) of 1,1,1,3,3,3-hexafluoro-2-(3-vinyl-phenyl)-propan-2-ol were dissolved in 50 ml of anhydrous DMF, and a spatula tip of 2-tert-butyl-hydroquinone (10 mg) was added for stabilization. 1.5 g (50 mmol) of sodium hydride were then added while stirring and cooling with ice at about 5° C. After everything had dissolved, 9.92 g (47mmol) of 4-chlorobenzenesulfonyl chloride were added at the same temperature. The mixture was stirred for 72 hours at room temperature, methylene chloride was then added and the mixture was washed with water, dried, filtered and evaporated down. The residue obtained was chromatographed with hexane/chloroform over a silica gel column. 16.65 g of 2-(4-chlorobenzenesulfonyloxy)-1,1,1,3,3,3-hexafluoro-2-(3-vinylphenyl)-propane (=2,2,2-trifluoro-1-trifluoromethyl-1-(3-vinylphenyl)-ethyl 4-chlorobenzenesulfonate) were isolated (colorless crystals, m.p.: 70° C.).

Workup

  1. dissolutionAfter everything had dissolved
  2. stirringThe mixture was stirred for 72 hours at room temperature
  3. washthe mixture was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated down
  7. customThe residue obtained
  8. customwas chromatographed with hexane/chloroform over a silica gel column

Sources & evidence

ORD record
ord-35b143657e314a13bb1bf547fac25e94
Source dataset
uspto-grants-1998_02
Patent number
US05716756

Reaction notes

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