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

HRID 2202168Notes

Reaction equation

HRID 2202168 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-fd23bfd47cd649b6b4b95318cb269300
Source dataset
uspto-grants-2016_06
Patent number
US09365529B2

Reaction notes

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