Benzenesulfonyl chloride → 1-Fluoro-2-fluoromethyl-3-butyn-2-yl benzenesulfonate

HRID 1282433Notes

Reaction equation

HRID 1282433 reaction equation
[F:1][CH2:2][C:3]([CH2:7][F:8])([OH:6])[C:4]#[CH:5].[C:9]1([S:15](Cl)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[H-].[Na+].CCCCCC.CCOCC>O1CCCC1>[C:9]1([S:15]([O:6][C:3]([CH2:7][F:8])([C:4]#[CH:5])[CH2:2][F:1])(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 184244281-Fluoro-2-fluoromethyl-3-butyn-2-olHCID 21584099Diethylether hexane

Product 1

HCID 184244191-Fluoro-2-fluoromethyl-3-butyn-2-yl benzenesulfonateYield 84.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An amount (1.2 g) of 1-fluoro-2-fluoromethyl-3-butyn-2-ol and benzenesulfonyl chloride (1.8 g) were dissolved in tetrahydrofuran (10 ml); to the solution under cooling with ice, 60% oily sodium hydride (0.48 g) was added in a nitrogen atmosphere. After the end of the addition, the mixture was stirred for 4 hours while its temperature was raised to room temperature. A hexane/ether mixed solvent (1/1) was added to the reaction mixture, which was then washed with water and a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane/methylene chloride=1/1) to give the titled compound (2.2 g).

Workup

  1. additionwas added in a nitrogen atmosphere
  2. additionAfter the end of the addition
  3. washwas then washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0d87ca2e77634e038784d875e3edd0c7
Source dataset
uspto-grants-2002_09
Patent number
US06455708B1

Reaction notes

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