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ChemicalBook CAS DataBase List 4-Iodo-1-[(4-Methoxyphenyl)Methyl]-1H-Pyrazole

4-Iodo-1-[(4-Methoxyphenyl)Methyl]-1H-Pyrazole synthesis

3synthesis methods
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Yield:905751-58-8 93%

Reaction Conditions:

Stage #1: 4-iodopyrazolewith sodium hydride in N,N-dimethyl-formamide at 0 - 20;
Stage #2: p-methoxybenzyl chloride in N,N-dimethyl-formamide; for 2 h;

Steps:

1.a.i

To a stirred solution of 4-iodo-lH-pyrazole (1.50 g, 7.73 mmol) in dry DMF (15 niL) at 00C was added sodium hydride (9.28 mmol, 60% dispersion in mineral oil) and the reaction mixture was allowed to warm to room temperature. After the evolution of hydrogen had ceased, 4-methoxy-benzyl chloride (1.06 mL, 7.80 mmol) was added and the reaction was stirred for 2 h and then quenched with water (50 mL) and extracted with diethyl ether (100 mL). The organic layer was washed with water (3 x 30 mL) and brine, dried over magnesium sulphate and the solvent removed under vacuum. The crude residue was washed with small portions of hexane and dried in vacuo, providing the product as a EPO white solid (2.26 g, 93% yield). 1H-NMR (CDCl3) δ 7.51 (s, IH), 7.34 (s, IH), 7.17 (d, J= 8.5 Hz, 2H), 6.87 (d, J= 8.5 Hz, 2H), 5.21 (s, 2H), 3.78 (s, 3H).

References:

WO2006/84338,2006,A1 Location in patent:Page/Page column 61-62