Triethylamine → 1,4-Di-[(methanesulfonyl)oxy]-2-[((methanesulfonyl)oxy)methyl]benzene

HRID 412164Notes

Reaction equation

HRID 412164 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][C:7]=1[CH2:17][OH:18])(=[O:4])=[O:3].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][C:7]=1[CH2:17][O:18][S:27]([CH3:26])(=[O:29])=[O:28])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 185360451,4-Di-[(methanesulfonyl)oxy]-2-(hydroxymethyl)benzene

Product 1

HCID 185361361,4-Di-[(methanesulfonyl)oxy]-2-[((methanesulfonyl)oxy)methyl]benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Step B (13.6 g, 45.9 mmol) in 100 mL of dichloromethane at 0° C. was added triethylamine (12.8 mL, 92.1 mmol), followed by dropwise addition of methanesulfonyl chloride (4.30 mL, 55.6 mmol). After 20 minutes, the solution was concentrated in vacuo, then partitioned between EtOAc and saturated NaHCO3 solution. The organic layer was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was isolated as a brown solid which was used without further purification.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. custompartitioned between EtOAc and saturated NaHCO3 solution
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was isolated as a brown solid which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-44def723aa6b40438f6ca9d6748b3d0d
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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