Water → Ethyl 3-(2'-fluoro-5'-hydroxyphenyl)propionate
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].B(Br)(Br)Br.O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -15 °C
Procedure
To a solution of ethyl 3-(2-fluoro-5-methoxyphenyl)propanoate (100 mg) in dichloromethane (3.0 mL) was added dropwise a 1.0 M solution of boron tribromide in dichloromethane (0.15 mL) at −15° C., and the mixture was stirred at −15° C. for 5 hr. Water (20 ml) was added dropwise to the reaction mixture, and the mixture was extracted with dichloromethane. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (60 mg) as a colorless oil. This compound was used for the next step without further purification.
Workup
- extractionthe mixture was extracted with dichloromethane
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-26afe13a7675468eb13611797f096131
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181186B2
Reaction notes
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