2-Hydroxy-3-(naphthalen-2-yl)-5-nitrobenzaldehyde synthesis

Yield:1197212-87-5 16%

Reaction Conditions:

with sodium carbonate;tetrakis(triphenylphosphine) palladium⁽⁰⁾ in 1,2-dimethoxyethane;ethanol;water at 80; for 6 h;

Steps:

3

Example 3Synthesis of 3-(2-naphthyl)-2-hydroxy-5-nitro-benzaldehyde - compound 7 1 6 73-Bromo-2-hydroxy-5-nitro-benzaldehyde (1 ) (2.Og, 0.008 mole) and 2-naphthyl boronic acid (6) (1.68g, 0.0097 mole) were dissolved in 30ml of 1 ,2-dimethoxyethane (DME). Ethanol (20 ml) and water (4ml) was added to the above reaction mixture followed by the addition of Na₂CC>3 (3.44g, 0.0325 mole). The reaction mixture was stirred at 80⁰C for 6h. Reaction mixture was cooled to room temperature and acidified with dilute ice cold hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over dry sodium sulphate and concentrated to get solid. This solid was recrystallized using dichloromethane: EtOH (80:20) to obtain pure compound 7. Yield=0.380g (16%) M. P. = 193-201 ⁰C¹H NMR (CDCI₃) δ (ppm) = 12.2 (s, 1 H), 10.07 (s, 1 H), 8.62 (d, J=17.94 Hz, 2H), 7.77-8.09 (m, 7H)

References:

WO2009/141236,2009,A1 Location in patent:Page/Page column 8