4-Chlorotoluene → 4-Methylbiphenyl

Participants

Reaction Steps

The general procedure from Example 9 was followed using 4-methylchlorobenzene (152 mg, 1.2 mmol) and PhB(OH)2 (1.2 mmol) with Pd2(dba)3 (20 mg, 0.0218 mmol) and (Me3C)2PH(O) from Experiment 2 (14.5 mg, 0.0878 mmol) and CsCO3 (651 mg, 2.0 mmol) in 4.0 mL of 1,4-dioxane. After 24 h, the reaction mixture was chromatographed with 5% ethyl acetate/hexane to give 127 mg (63% yield) of 4-phenyltoluene. It was >95% pure by 1H NMR and GC/MS. 1H NMR (500 MHz, CDCl3): δ 7.74 (d, J=7.50 Hz, 2H), 7.65 (d, J=8.05 Hz, 2H), 7.57 (m, 2H), 7.47 (m, 1H), 7.40 (m, 2H), 2.54 (s, 3H) ppm. 13C NMR (125 MHz, CDCl3): δ 141.1, 138.3, 136.9, 129.4, 128.6, 126.9, 126.8, 21.0 ppm.

Provenance & Evidence