Bromobenzene → 4-Methoxybiphenyl

HRID 412806Notes

Reaction equation

HRID 412806 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.[F-].[K+]>C1COCC1>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 201262(4-Methoxyphenyl)boronic acidHCID 522689Potassium Fluoride

Product 1

HCID 119434-MethoxybiphenylYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Bromobenzene (79 mg, 0.50 mmol) reacted with 4-methoxyphenylboronic acid (99 mg, 0.65 mmol) using 1 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and KF (87 mg, 1.50 mmol) in THF solvent at room temperature to give the title compound (87 mg, 95%) as a white solid. The reaction of 4-chloroanisole (71 mg, 0.50 mmol) with phenylboronic acid (92 mg, 0.75 mmol) gave the title compound (74 mg, 80%) using 1/2 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and KF in THF solvent at 40° C. 1H-NMR (400 MHz, CDCl3): δ 7.61 (m, 4H), 7.48 (t, 2H, J=7.6 Hz), 7.37 (app.t, 1H, J=7.2 Hz), 7.04 (d, 2H, J=8.8 Hz), 3.90 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 159.09, 140.76, 133.69, 128.66, 128.08, 126.67, 126.60, 114.14, 55.26. GC/MS(EI): m/z 184 (M+). Anal. Calcd for C13H12O: C, 84.75; H, 6.56. Found: C, 84.86; H, 6.76.

Workup

  1. customat room temperature

Sources & evidence

ORD record
ord-881097e948954a1d8eb4d403f7430e73
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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