3'-CHLORO-BIPHENYL-2-CARBALDEHYDE synthesis

6synthesis methods

Product Name:3'-CHLORO-BIPHENYL-2-CARBALDEHYDE
CAS Number:216443-25-3
Molecular formula:C13H9ClO
Molecular Weight:216.66

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Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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216443-25-3
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Yield: 43%

Reaction Conditions:

Stage #1:1-bromo-3-chlorobenzene;N-tert-butyl-1-(2-methoxyphenyl)methanimine with chromium dichloride;magnesium in tetrahydrofuran at 20; for 12 h;Inert atmosphere;Schlenk technique;
Stage #2: with hydrogenchloride in tetrahydrofuran at 20; for 0.5 h;Inert atmosphere;Schlenk technique;regioselective reaction;

Steps:

Biphenyl-2-carbaldehyde (3a)
General procedure: In a dried Schlenk tube were placed an ortho-methoxy-bearing aromatic aldimine 1 (0.2 mmol), Mg (11 mg, 0.44 mmol) and CrCl2 (3 mg, 0.02 mmol), then aryl bromide (0.4 mmol)was added by a syringe under atmosphere of nitrogen. After that, 2 ml THF was added and themixture was stirred at room temperature for 12 h. After quenched by 3 N HCl (1 mL), theresulting mixture was further stirred at room temperature for another 0.5 h, and then extractedwith ethyl acetate (3 x 10 mL). The combined organic layer was dried over anhydrous Na2SO4and concentrated under vacuum. The crude product was purified by silica gel chromatographyto afford the desired product 3.

References:

Tang, Jinghua;Luo, Meiming;Zeng, Xiaoming [Synlett,2017,vol. 28,# 19,p. 2577 - 2580] Location in patent:supporting information

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