1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 3-(4-Chlorothiazol-2-yl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of commercially available 2,4-dichlorothiazole (800 mg; 5.19 mmol), (3-formylphenyl)boronic acid (833 mg; 5.56 mmol), potassium phosphate tribasic K3PO4 (3.308 g; 15.60 mmol), Xantphos (75 mg; 0.13 mmol), and Pd(OAc)2 (29 mg; 0.13 mmol) in anh. THF (26 ml) was heated to 60° C., under nitrogen, for 3 h. After cooling to rt, the mixture was filtered over celite, and the separated solids were washed with DCM. Concentration to dryness under reduced pressure, and subsequent purification by FC (DCM) afforded 3-(4-chlorothiazol-2-yl)benzaldehyde as a colorless solid. LC-MS (conditions A): tR=0.77 min.; [M+H]+: 224.03 g/mol.

Provenance & Evidence