Potassium Carbonate → 3,5-Bis(4-cyanophenoxy)benzoic acid ethyl ester

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Reaction Steps

Potassium carbonate 0.611 g (4.4 mmol) was added to a stirred solution of 3,5-dihydroxy-benzoic acid ethyl ester 0.5 g (1.7 mmol) dissolved in 15 ml of DMF and stirred for 10 min. This was followed by dropwise addition of 4-fluorobenzonitrile 0.82 g (6.8 mmol), dissolved in 5 ml of DMF, and the contents of the flask were stirred at 80° C. for 4 h. The reaction mixture was poured into ice-cold water, and extracted with ethyl acetate. The organic phase was washed with Na2CO3 and saturated brine solution, dried over sodium sulphate and concentrated to afford an oily residue which was purified by column chromatography using hexane-ethyl acetate (10:2) to afford 0.4 g of the required product. The yield was 0.6 g. 1H NMR (DMSO-d6): δ 1.30 (3H, t), 4.30 (2H, q), 7.25 (2H, d), 7.32 (1H, t), 7.46 (2H, d), 7.90 (2H, d).

Provenance & Evidence