Toluene → 2,5-Dimethyl-4'-chlorobiphenyl

Participants

Reaction Steps

2-Bromo-m-xylene (77 mg, 0.42 mmol) reacted with 4-chlorophenylboronic acid (94 mg, 0.60 mmol) using 1/2 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and K3PO4 (254 mg, 1.20 mmol) in toluene at 100° C. to give the title compound (85 mg, 95%) as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 7.27 (d, 2H, J=8.0 Hz), 7.14 (d, 2H, J=8.0 Hz), 7.06 (d, 1H, J=7.6 Hz), 6.98 (bs, 1H), 6.92 (s, 1H), 2.25 (s, 3H), 2.11 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 140.44, 135.30,132.66, 132.04, 130.46, 130.33, 128.23, 128.18, 20.88, 19.88. GC/MS(EI): m/z 216 (M+), 181, 166, 89.

Provenance & Evidence