Water → 2-Chloro-6-fluorophenethyl methanesulfonate
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][CH2:10][OH:11].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21].O>ClCCl>[CH3:19][S:20]([O:11][CH2:10][CH2:9][C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:22])=[O:21]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-(2-chloro-6-fluorophenyl)ethanol (500 mg, 2.87 mmol), was dissolved in dichloromethane (20 mL), and triethylamine (870 mg, 8.61 mmol) was added to the reaction mixture. The solution was cooled to 0° C. and methanesulfonyl chloride (492 mg, 4.31 mmol) was added slowly. After the addition was complete, the reaction was stirred at 0° C. for 15 min and at room temperature for 4 hours. Water was slowly added and the solution was extracted with dichloromethane. The organic layer was washed with brine, and dried over sodium sulfate and concentrated in vacuo to give the residue 2-chloro-6-fluorophenethyl methanesulfonate (52) as a clear oil.
Workup
- additionAfter the addition
- extractionthe solution was extracted with dichloromethane
- washThe organic layer was washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-90a19e7287a34f97bebe1f708b285b3e
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08703776B2
Reaction notes
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