Toluene → 1-(4'-Methyl[1,1'-biphenyl]-2-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

A solid mixture of 4-methylphenylboronic acid (204 mg, 1.5 mmol), CsF (456 mg, 3.0 mmol), Pd(dba)2 (3 mg, 5 μmol), and ligand 1 (5 mg, 15 μmol) was thoroughly evacuated and purged with argon. 2′-Chloroacetophenone (0.13 mL, 1.0 mmol) and toluene (4 mL) were added and the reaction was heated at 110° C. for 1 h. GC-MS analysis indicated the reaction to be complete, i.e. starting aryl chloride reagent was completely consumed (quantitative GC yield). The reaction was taken up in ether (100 mL) and washed with H2O (30 mL) and brine (30 mL), The organic phase was dried over MgSO4, filtered and concentrated under vacuum. The crude product was purified by column chromatography on silica gel using hexanes:ethyl acetate (8:1) as eluant to afford the title compound as a yellow oil (198 mg, 92% isolated yield) after drying under vacuum. TON≈100 and TOF≈100. 1 H NMR (CDCl3): δ7.52 (d, J=8.4, 1H, ArH), 7.47 (d, J=7.2, 1H, ArH), 7.38 (t, J=7.2, 2H, ArH), 7.22 (s, 4H, ArH), 2.39 (s, 3H, C(O)CH3), 2.00 (s, 3H, ArCH3). 13C{1H} NMR (CDCl3): δ205.1, 140.9, 140.5, 137.8, 137.7, 130.6, 130.2, 129.4, 128.7, 127.8, 127.2, 30.4, 21.2.

Provenance & Evidence