Boron tribromide → HCID 73035483, compound

HRID 907520Notes

Reaction equation

HRID 907520 reaction equation
[CH2:1]([C:5]1[CH2:9][CH2:8][C:7](=[N:10][OH:11])[C:6]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18]C)=[C:14]([F:20])[CH:13]=1)[CH2:2][CH2:3][CH3:4].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl.CCCCCC>[CH2:1]([C:5]1[CH2:9][CH2:8][C:7](=[N:10][OH:11])[C:6]=1[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([F:20])[CH:13]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 73001449HCID 73001449, compound

Product 1

HCID 73035483HCID 73035483, compoundYield 57.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of 20 mg 3-butyl-2-(3-fluoro-4-methoxyphenyl)-2-cyclopenten-1-one oxime (Example 40) in 5 ml dichloromethane, was added 0.5 ml 1.0 M boron tribromide in hexane at 0° C. under inert atmosphere. The reaction mixture was stirred for 2 hours, poured into saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and filtered. Then the filtrate was concentrated under reduced pressure and purified by column chromatography (silica gel, hexane/ethyl acetate=2:1) to yield 11 mg 3-butyl-2-(3-fluoro-4-hydroxyphenyl)-2-cyclopenten-1-one oxime. Spectral data for Example 41 are provided along with the melting point in Table 4.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThen the filtrate was concentrated under reduced pressure
  6. custompurified by column chromatography (silica gel, hexane/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-b06b16a2bcd34b89a7bcb7d7098273b5
Source dataset
uspto-grants-2011_09
Patent number
US08013187B2

Reaction notes

Loading…