Boron tribromide → HCID 136146569, compound
Reaction equation
[F:1][C:2]1[C:7]([O:8]C)=[CH:6][CH:5]=[C:4]([F:10])[C:3]=1[C:11]1[NH:15][C:14](=[O:16])[O:13][N:12]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([F:10])[C:3]=1[C:11]1[NH:15][C:14](=[O:16])[O:13][N:12]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of 3-(2,6-difluoro-3-methoxyphenyl)-4H-[1,2,4]oxadiazol-5-one (0.09 g, 0.39 mmol) in DCM (3 ml) was cooled to −78° C. followed by addition of BBr3 (0.10 ml, 1.18 mmol). The reaction mixture was stirred at 25° C. for 2 h. After the completion of the reaction mixture (TLC monitoring), solution of NaHCO3 (20 ml) was added at 0° C. and extracted with ethyl acetate (3×50 ml). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by column chromatography on silica (60-120 M) using ethyl acetate/hexane (50:50) as the eluent to provide the title compound as white solid (0.08 g, 95%).
Workup
- extractionextracted with ethyl acetate (3×50 ml)
- washThe combined organics was washed with water, brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customThe crude residue was purified by column chromatography on silica (60-120 M)
Sources & evidence
- ORD record
- ord-c6cefd81fa974994b69d69679d36809b
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415383B2
Reaction notes
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