Sodium Carbonate → 2'-Hydroxy-3'-phenyl-5'methylacetophenone

Participants

Reaction Conditions

Reaction Steps

2′-Hydroxy-3′-bromo-5′methylacetophenone 233 (0.46 g, 2 mmol) and phenylboronic acid (0.24 g, 1 eq.) are dissolved in DME (10 ml) and placed under a nitrogen atmosphere. Na2CO3 (0.50 g, 3 eq.) in water (10 ml) is added, followed by Pd(Ph3)4 (0.12 g, 0.05 eq.) and the reaction mixture heated to 75° C. for 12-18 h. Most of the DME is removed in vacuo and the reaction mixture is diluted with ether, washed with water, brine, and dried (MgSO4), and concentrated in vacuo to give an oil. Purification by flash chromatography (5/95 EtOAc/hexanes) afforded 2′-Hydroxy-3′-phenyl-5′methylacetophenone 234 as a yellow solid (0.32 g, 71% yield) (Example 519, Table IIIa).

Provenance & Evidence