Triethylamine → 2,2-Difluoropropane-1,3-diyl dimethanesulfonate

HRID 570128

Reaction equation

HRID 570128 reaction equation
[F:1][C:2]([F:7])([CH2:5][OH:6])[CH2:3][OH:4].C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl>[CH3:15][S:16]([O:4][CH2:3][C:2]([F:7])([F:1])[CH2:5][O:6][S:16]([CH3:15])(=[O:18])=[O:17])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 957442,2-Difluoropropane-1,3-diol

Product 1

HCID 2428712,2-Difluoropropane-1,3-diyl dimethanesulfonateYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5 g (44.6 mmol) 2,2-difluoropropane-1,3-diol (prepared as described in J. Med. Chem. 1994, 37, 1857-1864) in DCM (50 mL) was added triethylamine (18.6 mL, 133.83 mmol) and methane sulphonyl chloride (6.9 mL, 89.22 mmol) at 0° C. and stirred for 1 h at 0° C. Thereafter the reaction mixture was quenched with water and extracted with DCM. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 2,2-difluoropropane-1,3-diyl dimethanesulfonate (9 g, 84%) which was used immediately in the next step.

Workup

  1. customThereafter the reaction mixture was quenched with water
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6897520d27f9497e907addb4497dad07
Source dataset
uspto-grants-2015_05
Patent number
US09023844B2

Linked notes

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