tert-butyl 4-(bromomethyl)-1H-pyrazole-1-carboxylate synthesis
- Product Name:tert-butyl 4-(bromomethyl)-1H-pyrazole-1-carboxylate
- CAS Number:530144-72-0
- Molecular formula:C9H13BrN2O2
- Molecular Weight:261.12
199003-22-0
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Yield:530144-72-0 80%
Reaction Conditions:
with carbon tetrabromide;triphenylphosphine in dichloromethane at 0 - 20; for 3 h;Inert atmosphere;
Steps:
2.1.1. tert-Butyl 4-(bromomethyl)-1H-pyrazole-1-carboxylate (33)
To a solution of tert-butyl 4-(hydroxymethyl)-1H-pyrazole-1-carboxylate (4.07 g, 20.5 mmol) in DCM (30 mL) was added triphenylphosphine (5.65 g, 21.6 mmol) at 0 °C, followed by dropwise addition of a solution of CBr4 (7.15 g, 21.6 mmol) in DCM (10 mL). The reaction was gradually warmed to rt and stirred for 3h. The reaction mixture was concentrated. The residue was purified by silica gel chromatography, eluted with EtOAc/hexanes from 0 to 30% to give the title compound (33, 4.26 g, 80 %). MS(ESI) m/z 206.9 (M+H-tBu)+.
References:
Hu, Carol H.;Neissel Valente, Meriah W.;Halpern, O. Scott;Jusuf, Sutjano;Khan, Javed A.;Locke, Gregory A.;Duke, Gerald J.;Liu, Xiaoqin;Duclos, Franck J.;Wexler, Ruth R.;Kick, Ellen K.;Smallheer, Joanne M. [Bioorganic and Medicinal Chemistry Letters,2021,vol. 42,art. no. 128010] Location in patent:supporting information
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