3-(3-Bromophenyl)-1-methyl-1H-pyrazole synthesis
- Product Name:3-(3-Bromophenyl)-1-methyl-1H-pyrazole
- CAS Number:425379-68-6
- Molecular formula:C10H9BrN2
- Molecular Weight:237.1
948294-12-0
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Yield:425379-68-6 99%
Reaction Conditions:
Stage #1: 3-(3-bromo-phenyl)-1H-pyrazolewith sodium hydride in tetrahydrofuran at 0; for 0.5 h;
Stage #2: methyl iodide in tetrahydrofuran at 20; for 4 h;
Steps:
46.3 Step 3: 3-(3-Bromo-henyI)-1 -methyl-i H-yrazole
3-(3-Bromo-phenyl)-1 H-pyrazole (17 g; 60.97 mmol; 1.00 eq.) dissolved in THF (5 mL)was added dropwise to a suspension of Sodium hydride (2.44 g; 60.97 mmol; 1 .00eq.) in THF (500 mL) maintained at 0°C. The reaction mixture was stirred for 30 mmbefore the dropwise addition of lodomethane (8.03 mL; 122 mmol; 2.00 eq.). It wasthen allowed to warm to RT and stirred for another 4h. Ice was added to quench thereaction and the mixture was extracted with ethyl acetate (30 mL x 2). Combinedorganic layers were dried over anhydrous sodium sulfate, filtered and concentrated togive the title compound as a brown liquid (14.5 g, 99%). LC/MS: (max plot) 99 %;(254nm) 99%; Rt 4.1 mm; 239.0 (M+1).
References:
WO2015/106058,2015,A1 Location in patent:Page/Page column 119
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