4-Chloroanisole → 4-o-Tolylanisole

HRID 412818Notes

Reaction equation

HRID 412818 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.[F-].[K+]>C1(C)C=CC=CC=1>[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 121674-ChloroanisoleHCID 522689Potassium FluorideHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 103527084-o-TolylanisoleYield 100.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Chloroanisole (74 mg, 0.52 mmol) reacted with 2-methylphenylboronic acid (102 mg, 0.75 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 (104 mg, 99%) as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 7.35-7.31 (m, 6H), 7.04 (d, 2H, J=8.8 Hz), 3.92 (s, 3H), 2.37 (s, 3H). 13C{1H}-NMR (125 MHz, CDCl3): δ 158.43, 141.47, 135.40, 134.28, 130.25, 130.19, 129.85, 126.91, 125.71, 113.41, 55.19, 20.52. GC/MS(EI): m/z 198 (M+).

Workup

  1. customat 80° C.

Sources & evidence

ORD record
ord-f092b514a7df4e1986360ca7d5f33dcd
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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