3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile synthesis
- Product Name:3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
- CAS Number:1212021-11-8
- Molecular formula:C13H15BClNO2
- Molecular Weight:263.53
289039-30-1
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Yield: 20%
Reaction Conditions:
with potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 in 1,4-dioxane for 4 h;Inert atmosphere;Reflux;
Steps:
35
Intermediate 353-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile; A suspension of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (665 mg, 2.62 mmol), 3-chloro-5-iodobenzonitrile (345 mg, 1.31 mmol), and potassium acetate (386 mg, 3.93 mmol) in dioxane (5 mL) was degassed with a stream of argon for a couple of min. PdCl2(dppf) CH2Cl2 (53.5 mg, 0.07 mmol) was added and the mixture was heated at reflux under N2 for 4 h. The mixture was allowed to cool and was then filtered. The filter cake was washed with EtOAc. The filtrate was concentrated in vacuo. The residue was purified by flash chromatography (eluent: heptane/EtOAc gradient) affording the title compound (69 mg, 20% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.30 (s, 12H), 7.88 (dd, 1H), 7.90-7.94 (m, 1H), 8.19 (dd, 1H); MS (CI) m/z 264 [M+H]+.Note: the product has no UV-response but is visualized on TLC by a visualization agent containing phosphomolybdic acid and Ce(SO4)2.
References:
ASTRAZENECA AB US2012/165347, 2012, A1 Location in patent:Page/Page column 30-31
766-84-7
278 suppliers
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73183-34-3
589 suppliers
$6.00/5g
1212021-11-8
62 suppliers
$45.00/25mg