Boron tribromide → HCID 66685850, compound

HRID 922264Notes

Reaction equation

HRID 922264 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[C:11]([O:13]C)[CH:10]=[CH:9][C:8]=2[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:5]([CH3:22])[O:4][N:3]=1.B(Br)(Br)Br>ClCCl>[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:8]=2[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:5]([CH3:22])[O:4][N:3]=1

Participants

4

Conditions

Temperature
0 °C

Procedure

To a 25 mL RB flask fitted with magnetic stirrer was charged with 10 mL of dichloromethane. To the stirred solvent was added ethyl 3-[2-(3,5-dimethyl-1,2-oxazol-4-yl)-4-methoxy phenyl]propanoate (0.120 g, 0.4 mmol). The reaction mixture was cooled to 0° C. and boron tribromide (0.099 g, 0.4 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 (0.1 g, yield: 90.90%).

Workup

  1. customTo a 25 mL RB flask fitted with magnetic stirrer
  2. customthe reaction mixture was quenched with ethanol (1 mL) at 0° C. by slow addition
  3. concentrationThe reaction mixture was concentrated
  4. distillationto distill off the solvent
  5. additionethyl acetate (10 mL) was added
  6. washThe organic layer was washed with saturated NaHCO3 solution (10 mL)
  7. dry with materialThe organic layer was dried over anhydrous Na2SO4
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c7314b5d76f2415383f4aa3ad66397e1
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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