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

Reaction equation

Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[Cl:10][C:11]1[CH:16]=[CH:15]C(B(O)O)=[CH:13][CH:12]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:28]1(C)C=CC=CC=1>>[CH3:28][C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:2][C:3]=1[C:9]1[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][CH:13]=1

Participants

Reactant 4

HCID 1140Toluene

HCID 62657Potassium Phosphate, Tribasic

HCID 684712-Bromo-m-xylene

HCID 742994-Chlorophenylboronic acid

Product 1

HCID 185393302,5-Dimethyl-4'-chlorobiphenylYield 95%

Procedure

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.