Phosphorus tribromide → 1-[4'-(4-Bromomethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester
Reaction equation
P(Br)(Br)[Br:2].[CH2:5]([O:7][C:8]([C:10]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[O:29][N:28]=[C:27]([CH3:30])[C:26]=4[CH2:31]O)=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:9])[CH3:6].C([O-])(O)=O.[Na+]>COCCOC>[CH2:5]([O:7][C:8]([C:10]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[O:29][N:28]=[C:27]([CH3:30])[C:26]=4[CH2:31][Br:2])=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:9])[CH3:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Phosphorus tribromide (0.43 mL, 4.53 mmol) was added to a solution of 1-[4′-(4-hydroxymethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (1.14 g, 3.02 mmol) in DME (30 mL) at 0° C. The reaction was stirred overnight at room temperature, and then cooled to 0° C. and neutralized with saturated aqueous NaHCO3 to pH 7. The mixture was partitioned between CH2Cl2 and H2O, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography to give the title compound.
Workup
- customThe mixture was partitioned between CH2Cl2 and H2O
- extractionthe aqueous layer was extracted with CH2Cl2
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customthe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-6be02ed72eda4be59be080bb114e44cd
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778983B2
Reaction notes
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