Methanol → Ethyl 3-(2-fluoro-4-hydroxyphenyl)propanoate
Reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]C)=[CH:9][C:8]=1[F:15])[CH3:2].B(Br)(Br)Br.CO>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[F:15])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
3-(2-Fluoro-4-methoxy-phenyl)-propionic acid ethyl ester (2.5 g, 11.05 mmol) obtained in Step B was dissolved in anhydrous DCM (10 mL). 1M BBr3 solution (33 mL, 33.15 mmol) was added thereto at −78° C., and the mixture was stirred at room temperature for 3 hours. After the termination of the reaction, MeOH was added to the reactant. The mixture was concentrated under reduced pressure and purified by column chromatography (eluent, EtOAc/Hex=1/2) to obtain the title compound (1.88 g, 80%).
Workup
- additionwas added to the reactant
- concentrationThe mixture was concentrated under reduced pressure
- custompurified by column chromatography (eluent, EtOAc/Hex=1/2)
Sources & evidence
- ORD record
- ord-f1c934f689f644d597e59916da2249f8
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447044B2
Reaction notes
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