1-Chloro-4-nitrobenzene → 4-Methoxy-4'-nitrobiphenyl

HRID 412801Notes

Reaction equation

HRID 412801 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.[F-].[K+]>C1COCC1>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 201262(4-Methoxyphenyl)boronic acidHCID 522689Potassium Fluoride

Product 1

HCID 111280794-Methoxy-4'-nitrobiphenylYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloronitrobenzene (164 mg, 1.04 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 at 50° C. for 17 h to give the title compound (234 mg, 98%) as a solid: 1H-NMR (400 MHz, CDCl3): δ 8.27 (d, 2H, J=8.76 Hz), 7.69 (d, 2H, J=8.76 Hz), 7.59 (d, 2H, J=8.70 Hz), 7.03 (d, 2H, J=8.71 Hz), 3.88 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 160.40, 147.15, 146.47, 130.99, 128.52, 127.01, 124.10, 114.56, 55.39. GC/MS(EI): m/z (M+).

Workup

  1. customat 50° C.
  2. customfor 17 h

Sources & evidence

ORD record
ord-765db51224a84d27a5735d6b337eae3d
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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