Triethylamine → 2-(2,4-Difluorophenyl)ethyl methanesulphonate
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[CH2:21][CH2:22][OH:23]>ClCCl>[CH3:1][S:2]([O:23][CH2:22][CH2:21][C:15]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=1[F:13])(=[O:4])=[O:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Methanesulphonyl chloride (3.3 ml; 0.043 mol) and triethylamine (5.9 ml; 0.043 mol) were added to a solution of 2-(2,4-difluorophenyl)ethanol (6.4 g; 0.0426 mol) in dichloromethane (100 ml). The solution was cooled for 1 h at 0° C. and then brought to room temperature for 1 h. The reaction mixture was then treated by washing, successively, with 5N sulphuric acid (20 ml), water (50 ml), a 5% solution of NaHCO3 (50 ml) and water (50 ml). The organic phase was then dried over Na2SO4, filtered and concentrated at reduced pressure. The residue was taken up twice in CCl4, thus obtaining 6.42 g of 2-(2,4-difluorophenyl)ethyl methanesulphonate.
Workup
- additionThe reaction mixture was then treated
- washby washing
- dry with materialThe organic phase was then dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated at reduced pressure
Sources & evidence
- ORD record
- ord-1ae1936b97a049c3bb1a06efe87e748e
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507528B2
Reaction notes
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