Hydrochloric Acid → Methyl 2-fluorophenylacetate
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].Cl.[CH3:13]O>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:13])=[O:10]Participants
4
Conditions
- Temperature
- 68 °C
Procedure
To a stirred solution of 2-fluorophenylacetic acid (9.6 g, 62 mmol) in MeOH (100 mL) was added concentrated HCl (0.7 mL, 19 mmol). The solution was heated at 68° C. for 4 hours, and then the reaction was concentrated in vacuo to remove MeOH. The residue was dissolved in ether and then washed with saturated NaHCO3 solution (1×50 mL). The organic extracts were separated, dried with Na2SO4, filtered and concentrated to give a yellow oil (10 g). MS m/e=169.0 (M+H)+.
Workup
- concentrationthe reaction was concentrated in vacuo
- customto remove MeOH
- dissolutionThe residue was dissolved in ether
- washwashed with saturated NaHCO3 solution (1×50 mL)
- customThe organic extracts were separated
- dry with materialdried with Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-2318df47945a4424883b3a2abe63af2c
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07635715B2
Reaction notes
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