Hydrochloric Acid → HCID 59370911, compound

HRID 1694767Notes

Reaction equation

HRID 1694767 reaction equation
[Cl:1][C:2]([F:10])([F:9])[C:3]([Cl:8])([F:7])[CH2:4][CH2:5]I.[F:11][C:12]([F:24])([F:23])[CH2:13][CH2:14][S:15]([CH2:18][C:19]([O:21][CH3:22])=[O:20])(=[O:17])=[O:16].[H-].[Na+].Cl>CS(C)=O>[Cl:8][C:3]([F:7])([C:2]([Cl:1])([F:10])[F:9])[CH2:4][CH2:5][CH:18]([S:15]([CH2:14][CH2:13][C:12]([F:23])([F:24])[F:11])(=[O:17])=[O:16])[C:19]([O:21][CH3:22])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 47126711,2-dichloro-1,1,2-trifluoro-4-iodobutaneHCID 57425720Methyl 2-(3,3,3-trifluoropropylsulfonyl)acetate

Product 1

HCID 59370911HCID 59370911, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 5.0 g of 1,2-dichloro-1,1,2-trifluoro-4-iodobutane and 3.8 g of methyl (3,3,3-trifluoropropylsulfonyl)acetate in 100 ml of dimethyl sulfoxide was added 0.7 g of sodium hydride (60% in oil) at room temperature, and the mixture was stirred at the same temperature for 3 days. To the reaction mixture was added 10% hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 1.50 g of methyl 5,6-dichloro-5,6,6-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate (hereinafter referred to as the present compound (1)).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0796ee2d2527497084644a92362b99b3
Source dataset
uspto-grants-2012_04
Patent number
US08158829B2

Reaction notes

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