Water → Methyl 3-cyclopropyl-3-(4-fluoro-3-hydroxyphenyl)propanoate

HRID 709668Notes

Reaction equation

HRID 709668 reaction equation
[CH:1]1([CH:4]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[C:12]([O:17]C)[CH:11]=2)[CH2:5][C:6]([O:8][CH3:9])=[O:7])[CH2:3][CH2:2]1.B(Br)(Br)Br.O>ClCCl>[CH:1]1([CH:4]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[C:12]([OH:17])[CH:11]=2)[CH2:5][C:6]([O:8][CH3:9])=[O:7])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 117759927Methyl 3-cyclopropyl-3-(4-fluoro-3-methoxyphenyl)propanoate

Product 1

HCID 117760257Methyl 3-cyclopropyl-3-(4-fluoro-3-hydroxyphenyl)propanoateYield 52.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 3-cyclopropyl-3-(4-fluoro-3-methoxyphenyl)propanoate (800 mg) in dichloromethane (20 mL) was added dropwise a 1.0 M solution of boron tribromide in dichloromethane (3.8 mL) at −5° C. over 20 min, and thereafter the mixture was stirred for 2 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 and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (400 mg) 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 obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2b6f54dff29d4329b4403277de65bf28
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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