Water → HCID 117760306, compound

HRID 709724Notes

Reaction equation

HRID 709724 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[C:7]([CH3:9])[CH:8]=1.B(Br)(Br)Br.O>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[C:7]([CH3:9])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 117760005HCID 117760005, compound

Product 1

HCID 117760306HCID 117760306, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

To a solution of ethyl 3-(3-methoxy-5-methylphenyl)propanoate (2.00 g) in dichloromethane (30 mL) was added a 1.0 M solution (13.5 mL) of boron tribromide in dichloromethane at −5° C., and the mixture was stirred at −5° C. for 2 hr. Water (20 mL) was added dropwise to the reaction mixture over 30 min, 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, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.00 g) as a yellow oil.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4b2af8ce527a4dd8b9abeee696fac32b
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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