3-Chloroanisole → 3,4'-Dimethoxybiphenyl

HRID 412830

Reaction equation

HRID 412830 reaction equation
Cl[C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.[F-].[K+]>C1(C)C=CC=CC=1>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 178333-ChloroanisoleHCID 201262(4-Methoxyphenyl)boronic acidHCID 522689Potassium Fluoride

Product 1

HCID 6118463,4'-DimethoxybiphenylYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Chloroanisole (76 mg, 0.54 mmol) reacted with 4-methoxyphenylboronic acid (117 mg, 0.77 mmol) using 1 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and KF (87 mg, 1.50 mmol) in toluene at 80° C. to give the title compound (112 mg, 97%) as a colorless oil: 1H-NMR (300 MHz CDCl3): δ 7.57 (d, 2H, J=8.7 Hz), 7.37 (t, 1H, J=7.8 and 8.1 Hz), 7.17 (m, 2H), 7.01 (d, 2H, J=8.7 Hz), 6.88-6.97 (m, 1H), 3.89 (s, 3H), 3.88 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 159.86, 159.17, 142.28, 135.51, 129.66, 128.13, 119.21, 114.09, 112.44, 111.93. GC/MS (EI): m/z 214 (M+), 199, 171, 128. Anal. Calcd for C14H4O2: C, 78.48; H, 6.59. Found C, 78.46: H, 6.62.

Workup

  1. customat 80° C.

Sources & evidence

ORD record
ord-036541a1dd9b438cad135b4c773f2dce
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Linked notes

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