ChemicalBook CAS DataBase List 2-(3-BROMOBENZOYL)PYRIDINE

2-(3-BROMOBENZOYL)PYRIDINE synthesis

5synthesis methods

Product Name:2-(3-BROMOBENZOYL)PYRIDINE
CAS Number:206357-82-6
Molecular formula:C12H8BrNO
Molecular Weight:262.1

109-04-6 Synthesis

109-04-6
528 suppliers
$6.00/25g

15930-59-3 Synthesis

15930-59-3
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$75.00/250mg

206357-82-6
21 suppliers
$478.00/1g

Yield:206357-82-6 80%

Reaction Conditions:

Stage #1: 2-bromo-pyridinewith isopropyl magnesium ⁽¹⁺⁾; bromide in tetrahydrofuran at 0 - 20;
Stage #2: 3-bromo-N,N-dimethylbenzamide in tetrahydrofuran at 20; for 49 h;

Steps:

synthesis of (3-Bromophenyl)(pyridin-2-yl)methanone

A 100 mL round-bottomed flask was charged with 2-bromopyridine (6.9 mL, 72.7 mmol) and isopropylmagnesium bromide (40 mL, 80 mmol, 2 M solution in THF) was added dropwise into the reaction mixture at 0° C.
After the addition was complete, the reaction was allowed to slowly warm to room temperature and stirred overnight.
The reaction mixture was used for the next step without purification.To a 250 mL round-bottomed flask was added pyridin-2-ylmagnesium bromide (13.3 g, 72.7 mmol) in THF (40 mL) to give a white suspension. 3-Bromo-N,N-diethylbenzamide (20.5 g, 80 mmol) in 50 mL of anhydrous THF was added into the reaction mixture over a period of 1 hour. The reaction mixture was stirred at room temperature for 48 hours and then quenched by adding cold saturated ammonium chloride aqueous solution. The mixture was extracted with toluene and the organic portion was subjected to column chromatography (SiO₂, 15% THF in hexanes) to yield 15.3 g (80%) of (3-bromophenyl)(pyridin-2-yl)methanone

References:

US9461254,2016,B2 Location in patent:Page/Page column 198-199