Ethanol → 2-(2-Fluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][C:10]=1[F:17])=[O:5])[CH3:2].B(Br)(Br)Br.CCO>C(Cl)Cl>[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[F:17])=[O:5])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
After 2-(2-fluoro-4-methoxy-phenyl)-cyclopropane carboxylic acid ethyl ester (0.16 g, 0.67 mmol) obtained in Step B was dissolved in anhydrous DCM (10 mL), 1M BBr3 solution (3.36 mL, 3.35 mmol) was added thereto at −78° C., and the mixture was stirred at room temperature for 3 hours. After the termination of the reaction, EtOH was added thereto, and the mixture was stirred at room temperature for 30 minutes. The reactant was concentrated under reduced pressure, added with saturated sodium bicarbonate aqueous solution, and extracted with DCM. The organic layer was concentrated under reduced pressure and purified by column chromatography (eluent, EtOAc/Hex=1/4) to obtain the title compound (0.25 g, 97%).
Workup
- additionwas added
- stirringthe mixture was stirred at room temperature for 30 minutes
- concentrationThe reactant was concentrated under reduced pressure
- additionadded with saturated sodium bicarbonate aqueous solution
- extractionextracted with DCM
- concentrationThe organic layer was concentrated under reduced pressure
- custompurified by column chromatography (eluent, EtOAc/Hex=1/4)
Sources & evidence
- ORD record
- ord-5fdb96adcc1046fdb94d6c1efe673154
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447044B2
Reaction notes
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