Boron tribromide → HCID 23136380, compound
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8]C)[C:5]([F:10])=[CH:4][C:3]=1[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([F:10])=[CH:4][C:3]=1[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a 25 mL RB flask fitted with magnetic stirrer was charged with 3 mL of dichloromethane. To the stirred solvent was added Ethyl 3-(2,5-difluoro-4-methoxyphenyl)propanoate (0.08 g, 0.327 mmol). The reaction mixture was cooled to 0° C. and boron tribromide (0.04 mL, 0.425 mmol) was added drop wise. After stirred for 30 minutes, the reaction mixture was quenched with ethanol (1 mL) at 0° C. by slow addition. The reaction mixture was concentrated to distill off the solvent; ethyl acetate (10 mL) was added. The organic layer was washed with saturated NaHCO3 solution (10 mL), followed by brine solution (10 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as colorless oil (0.06 g, yield: 80.0%).
Workup
- customTo a 25 mL RB flask fitted with magnetic stirrer
- customthe reaction mixture was quenched with ethanol (1 mL) at 0° C. by slow addition
- concentrationThe reaction mixture was concentrated
- distillationto distill off the solvent
- additionethyl acetate (10 mL) was added
- washThe organic layer was washed with saturated NaHCO3 solution (10 mL)
- dry with materialThe organic layer was dried over anhydrous Na2SO4
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-35c17e19d6cc4f3895cb8e4f9cdce230
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278915B2
Reaction notes
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