Oxalyl chloride → 4-But-2-ynyloxy-benzenesulfonyl chloride

HRID 1966095Notes

Reaction equation

HRID 1966095 reaction equation
[Na].[CH2:2]([O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([OH:16])(=O)=[O:14])=[CH:9][CH:8]=1)[C:3]#[C:4][CH3:5].C(Cl)(=O)C([Cl:20])=O>CN(C)C=O.ClCCl>[CH2:2]([O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([Cl:20])(=[O:16])=[O:14])=[CH:9][CH:8]=1)[C:3]#[C:4][CH3:5]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 5360545SodiumHCID 18612864HCID 18612864, compound

Product 1

HCID 111959284-But-2-ynyloxy-benzenesulfonyl chlorideYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

30 g (107 mmol) of the sodium salt of 4-but-2-ynyloxybenzenesulfonic acid in 120 ml of dimethylformamide are added dropwise to a solution of 28 ml (321 mmol) of oxalyl chloride in 120 ml of dichloromethane, cooled beforehand to −10° C., and then the reaction medium is stirred at ambient temperature for 18 h. 800 ml of ice are added and the medium is extracted with ethyl acetate. The organic phases are combined, washed with water, dried over magnesium sulfate, filtered and concentrated under vacuum. 22 g (84%) of 4-but-2-ynyloxybenzenesulfonyl chloride are obtained in the form of a beige solid.

Workup

  1. extractionthe medium is extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1a2735d23025452c85691ac544f15e31
Source dataset
uspto-grants-2013_04
Patent number
US08420632B2

Reaction notes

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