Acrylic acid, 2-(hydroxymethyl)-, ethyl ester → Ethyl 2-(fluoromethyl)prop-2-enoate
Reaction equation
O[CH2:2][C:3](=[CH2:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].CCN(S(F)(F)[F:16])CC>ClCCl>[F:16][CH2:2][C:3](=[CH2:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of ethyl 2-(hydroxymethyl)acrylate (3.0 g, 23.1 mmol) in dichloromethane (40 mL) cooled to −78° C., was added DAST (3.32 mL, 25.4 mmol). The reaction mixture was stirred at −78° C. for 30 minutes and then at ambient temperature for 1 hour. The reaction was quenched with water (40 mL) and the layers were separated. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure to afford ethyl 2-(fluoromethyl)acrylate (2.54 g, 83%).
Workup
- waitat ambient temperature for 1 hour
- customThe reaction was quenched with water (40 mL)
- customthe layers were separated
- washThe organic layer was washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-b1dbb6cf1f6f4545ae2e4781df294ef4
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889704B2
Reaction notes
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