Reaction #657310

Reaction equation

2,2-difluoropropane-1,3-diol

triethylamine

methane sulphonyl chloride

→

2,2-difluoropropane-1,3-diyl dimethanesulfonate

Yield 84.0%

Solvents

DCM

Conditions

Workup

1. 1
   OtherThereafter the reaction mixture was quenched with water
2. 2
   Extractionextracted with DCM
3. 3
   DryingThe organic layer was dried over anhydrous sodium sulphate
4. 4
   Concentrationconcentrated

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.

Source