Potassium Carbonate → 2-[4-(Methylsulfanyl)phenoxy]benzaldehyde

Participants

Reaction Conditions

Reaction Steps

2-Fluorobenzaldehyde (31.6 mL, 300 mmol) and 4-(methylmercapto)phenol (46.27 g, 330 mmol) were dissolved in DMF (500 mL) and potassium carbonate (62.2 g, 450 mmol) was then added. The mixture was heated at 100° C. for 12 h under a nitrogen atmosphere. After cooling to room temperature the mixture was evaporated to dryness, co-evaporated with toluene and then partitioned between ethyl acetate and water. The organic layer was separated, washed with water, dried (MgSO4) and evaporated to a brown oil of the desired aldehyde material (84.4 g) which was contaminated with ca 15% of starting phenol, but sufficiently pure to use directly in the next stage; δH(CDCI3, 400 MHz) 2.47 (3 H, s), 6.87 (1 H, d), 6.99 (2 H, m), 7.17 (1 H, m), 7.29 (2 H, m), 7.49 (1 H, m), 7.92 (1 H, d), 10.49 (1 H, s). If required the crude mixture can be purified by flash chromatography [SiO2; ethyl acetate/ hexanes (2→10%)] to obtain a pure sample of the desired aldehyde compound.

Provenance & Evidence