Sodium Carbonate → HCID 19430383, compound

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To a solution of 5-bromo-3-methyl-thiophene-2-carbaldehyde (1.00 g, 4.88 mmol) in ethylene glycol dimethyl ether (9 ml) was added phenylboronic acid (0.773 g, 6.34 mmol), 2M Na2CO3 solution (6.3 ml) and Pd(PPh3)4 [0.282 g, 0.24 mmol). The mixture was heated for 18 hours, cooled and the solvent removed at reduced pressure to leave a brown residue which was partitioned between water (15 ml) and dichloromethane (20 ml). The organic was separated, washed with water (2×5 ml), brine (10 ml), dried (MgSO4) and the solvent removed at reduced pressure to give a brown oil. Purification by flash column chromatography (6:1 petrol 40-60° C./ethyl acetate) gave the sub-title compound as a yellow oil (0.90 g, 91% yield): 1H NMR (400 MHz, CDCl3) δH 2.75 (3H, s), 7.25 (1H, s) 7.35-7.75 (5H, s), 10.05 (1H, s).

Provenance & Evidence