Water → 2-(5-Methyl-1,3,4-thiadiazol-2-yl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-5-methyl-1,3,4-thiadiazole (150 mg, 0.84 mmol) in 1,2-dimethoxyethane (5 mL) are added 2-formylphenylboronic acid (190 mg, 1.26 mmol), Pd(PPh3)4 (97 mg, 0.08 mmol) and Na2CO3 (sat., 0.10 mL) at room temperature. The solution is heated to 100° C. for 18 hours then cooled and poured into water and EtOAc. Layers are separated and the aqueous phase extracted with EtOAc (1×10 mL). The combined organics are dried (MgSO4), filtered and concentrated to give the crude product which is purified via flash chromatography (12 g silica gel, 5-60% EtOAc/hexanes). The product-containing fractions are combined and concentrated to give 2-(5-methyl-1,3,4-thiadiazol-2-yl)-benzaldehyde (100 mg, 58%) which is used without further purification.

Provenance & Evidence