1-Cyclohexene-1-carboxaldehyde, 2-(4-chlorophenyl)-5,5-diMethyl- synthesis

5synthesis methods

Product Name:1-Cyclohexene-1-carboxaldehyde, 2-(4-chlorophenyl)-5,5-diMethyl-
CAS Number:1202186-71-7
Molecular formula:C15H17ClO
Molecular Weight:248.75

1053265-66-9 Synthesis

2-BroMo-5,5-diMethylcyclohex-1-enecarbaldehyde

1053265-66-9
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1679-18-1 Synthesis

1679-18-1
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1-Cyclohexene-1-carboxaldehyde, 2-(4-chlorophenyl)-5,5-diMethyl-

1202186-71-7
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Yield:1202186-71-7 77%

Reaction Conditions:

with potassium carbonate;tetrakis(triphenylphosphine) palladium⁽⁰⁾ in 1,4-dioxane;water at 100; for 0.2 h;Inert atmosphere;Microwave irradiation;

Steps:

A

A suspension of 2-bromo-5,5-dimethylcyclohex- 1 -enecarbaldehyde(250 mg, 1.15 mmol), 4-chlorophenyl boronic acid (270 mg, 1.727 mmol) and Pd(Ph₃P)₄ (66.5 mg, 0.058 mmol) in dioxane (2.5 mL) was stirred at room temperature in a 5 mL microwave vial under an atmosphere of nitrogen. A solution of potassium carbonate (318 mg, 2.3 mmol) in water (0.3 mL) was added and the solution became clear. The vial was capped and heated to 100 °C for 12 minutes in a microwave. The reaction was cooled to room temperature, diluted with CH2CI2, filtered through a plug of Celite, andconcentrated. The crude residue was purified by flash chromatography on silica gel (0- 25% EtOAc/ heptanes) to afford 2-(4-chlorophenyl)-5,5-dimethyIcyclohex-l - enecarbaldehyde as a clear colorless oil (220mg, 77% yield).

References:

WO2011/29842,2011,A1 Location in patent:Page/Page column 59-60