Bromobenzene → [Diphenyl(4-pyridyl)]methanol
Reaction equation
[Mg].Br[C:3]1C=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]([C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[NH4+].[O:25]1CCC[CH2:26]1>>[C:10]1([C:9]2[C:19]([C:18]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:20][CH:21]=[CH:22][C:17]=2[CH2:26][OH:25])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1Participants
Procedure
A Grignard reagent was prepared from magnesium (0.21 g, 8.64 mmol) (Wako Pure Chemical Industries, Ltd.) and bromobenzene (1.35 g, 8.60 mmol) (Wako Pure Chemical Industries, Ltd.). 4-Benzoylpyridine (0.52 g, 28.4 mmol) (Wako Pure Chemical Industries, Ltd.) was dissolved in tetrahydrofuran (10 mL) (Wako Pure Chemical Industries, Ltd.), and the Grignard reagent was added dropwise, followed by stirring at room temperature for 5 hours. A saturated aqueous solution of ammonium chloride (Wako Pure Chemical Industries, Ltd.) was added to the reaction solution, and mixture was extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.). The organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (chloroform (Wako Pure Chemical Industries, Ltd.) as an eluent), to thereby obtain the title compound (0.72 g, 97% yield).
Workup
- extractionwas extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.)
- dry with materialThe organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-5f4e81eb6c9d44cca72f66321c991c50
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846012B2
Reaction notes
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