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2-Formyl-4-(4-methoxyphenyl)phenol synthesis

2synthesis methods
-

Yield: 83%

Reaction Conditions:

with tetrabutylammomium bromide;potassium acetate;palladium diacetate;tris-(o-tolyl)phosphine in N,N-dimethyl-formamide at 110; for 4 h;Inert atmosphere;

Steps:

Representative cross-coupling procedure
General procedure: An oven-dried Schlenk tube was charged with 2-iodophenol (1a) (0.75 mmol, 3 equiv.), Bi(p-tolyl)3 (0.25 mmol, 1 equiv.), PdCl2(PPh3)2 (0.0225 mmol, 0.09 equiv.), KOAc (1.5 mmol, 6 equiv.) and DMA (3 mL) under a N2 atmosphere. The mixture was stirred in an oil bath at 110 °C for 2 h. The contents were quenched at rt with water (10 mL) and extracted with ethyl acetate (30 mL). The organic extract was washed with brine and dried using MgSO4. The organic solvent was removed under reduced pressure to obtain the crude product. This was purified by silica gel chromatography using hexane/ethyl acetate as eluent and product 2a was obtained in 83% yield.

References:

Rao, Maddali L.N.;Meka, Suresh [Tetrahedron Letters,2020,vol. 61,# 8,art. no. 151512]