Boron tribromide → HCID 90418520, compound

HRID 2177151Notes

Reaction equation

HRID 2177151 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:16]([F:19])([F:18])[F:17])[C:4]=1[CH3:20].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:16]([F:17])([F:18])[F:19])[C:4]=1[CH3:20]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 90418249HCID 90418249, compound

Product 1

HCID 90418520HCID 90418520, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Into a 50-mL round-bottom flask (1 atm) purged and maintained with an inert atmosphere of nitrogen, was placed ethyl 3-[4-methoxy-3-methyl-2-(trifluoromethyl)phenyl]propanoate (210 mg, 0.72 mmol, 1.00 equiv), dichloromethane (2.0 mL). This was followed by the addition of BBr3 (1N in dichloromethane) (1.45 mL, 2.00 equiv) dropwise with stirring at −78° C. The resulting solution was warmed to room temperature (30° C.) and stirred for 2 h. The reaction progress was monitored by LCMS. The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with 3×10 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by TLC-Plate with petroleum ether/EtOAc=4:1. This resulted in 0.130 g (65%) of ethyl 3-[4-hydroxy-3-methyl-2-(trifluoromethyl)phenyl]propanoate as a yellow solid. Mass spectrum (ESI, m/z): Calcd. for C13H15P3O3, 275.1 (M−H). found 275.1.

Workup

  1. customInto a 50-mL round-bottom flask (1 atm) purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe resulting solution was warmed to room temperature (30° C.)
  4. stirringstirred for 2 h
  5. customThe reaction was then quenched by the addition of 10 mL of water
  6. extractionThe resulting solution was extracted with 3×10 mL of dichloromethane
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by TLC-Plate with petroleum ether/EtOAc=4:1
  10. customThis resulted in 0.130 g (65%) of ethyl 3-[4-hydroxy-3-methyl-2-(trifluoromethyl)phenyl]propanoate as a yellow solid

Sources & evidence

ORD record
ord-5c3d567b460f414e81eb6134b5e30c27
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

Loading…