Water → 1-Fluoromethyl-2-phenylethyl methanesulfonate
Reaction equation
[F:1][CH2:2][CH:3]([OH:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21].O>C(Cl)Cl>[CH3:19][S:20]([O:11][CH:3]([CH2:2][F:1])[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)(=[O:22])=[O:21]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 1-fluoromethyl-2-phenylethanol (1.0 g, prepared as described by Bergmann, et al. J. Chem. Soc. 1961, 3448–3452) in DCM (30 mL) at 0° C. under nitrogen was added triethylamine (1.36 mL) followed by dropwise addition of methanesulfonyl chloride (0.6 mL). The mixture was allowed to slowly warm to room temperature overnight. The reaction mixture was poured into water and extracted with EtOAc. The EtOAc extracts were washed with water and brine, dried over Na2SO4, and concentrated to dryness to give 1.3 g of the title compound. MS CI, (M++H)=233, (M++H−CH3SO3H)=138.
Workup
- extractionextracted with EtOAc
- washThe EtOAc extracts were washed with water and brine
- dry with materialdried over Na2SO4
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-aae4c9108dca44bcb8a4ad01d53a55fb
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07064143B1
Reaction notes
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