4-Hydroxybenzaldehyde → 5-(4-Formylphenoxy)thiophene-2-carbonitrile

Participants

Reaction Steps

Dissolve 5-fluorothiophene-2-carbonitrile (0.541 g, 4.25 mmol) and 4-hydroxybenzaldehyde (0.519 g, 4.25 mmol) in DMF (11 mL). Add K2CO3 (1.469 g, 10.6 mmol) and heat at 100° C. for 1.5 hours. Concentrate the reaction mixture. Take the solid up in ethyl acetate (100 mL) and wash with water (2×25 mL). Dry the organic layer over MgSO4, filter and concentrate. Purify by chromatography eluting with 30% ethyl acetate in hexanes to give the title compound: 1H NMR (CDCl3): 9.96 (s, 1H), 7.98 (dd, J=6.6, 2.2 Hz, 2H), 7.86 (d, J=4.0 Hz, 1H), 7.40 (d, J=2.2 Hz, 2H), 6.96 (d, J=4.0 Hz, 1H); HPLC [YMC-Pro pack C-18 (150×4.6 mm, S-5 microm), 0.05% TFA/acetonitrile in 0.05% TFA/water at 1.0 mL/min, 10-20% over 5 min, 20-95% over 18], tR=17.4 min, 98.1% purity.

Provenance & Evidence