4-Chlorobenzonitrile → [1,1'-Biphenyl]-4-carbonitrile, 4'-methoxy-

HRID 412800Notes

Reaction equation

HRID 412800 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.[F-].[K+]>C1COCC1>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 121634-ChlorobenzonitrileHCID 201262(4-Methoxyphenyl)boronic acidHCID 522689Potassium Fluoride

Product 1

HCID 93892[1,1'-Biphenyl]-4-carbonitrile, 4'-methoxy-Yield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chlorobenzonitrile (140 mg, 1.02 mmol) reacted with p-methoxyphenylboronic acid (200 mg, 1.32 mmol) using 1/2 mol % of Pd(OAc)2/Ph5FcP(t-Bu)2 and KF (182 mg, 3.00 mmol) in THF solvent to give the title compound (197 mg, 94%) as white solid after recrystallization from hexane: 1H-NMR (400 MHz, CDCl3): δ 7.70 (d, 2H, J=8.41 Hz), 7.65 (d, 2H, J=8.40 Hz), 7.55 (d, 2H, J=8.80 Hz), 7.02 (d, 2H, J=8.79 Hz), 3.88 (s, 3H). 13C{1H}-NMR (125 MHz, CDCl3): δ 160.18, 145.17, 132.52, 131.45, 128.31, 127.06, 119.04, 114.52, 110.07, 55.35. GC/MS(EI): m/z (M+).

Sources & evidence

ORD record
ord-73e0d0c9ecbf4fe4b31ad81f6796a4b4
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

Loading…