TERT-BUTYL 4-(BROMOMETHYL)BENZYLCARBAMATE synthesis
- Product Name:TERT-BUTYL 4-(BROMOMETHYL)BENZYLCARBAMATE
- CAS Number:187283-17-6
- Molecular formula:C13H18BrNO2
- Molecular Weight:300.19
123986-64-1
187283-17-6
General procedure for the synthesis of tert-butyl 4-(bromomethyl)benzylcarbamate from tert-butyl 4-(hydroxymethyl)benzylcarbamate: 4-(N-tert-butoxycarbonylaminomethyl)benzyl alcohol (250 mg, 1.1 mmol) was dissolved in tetrahydrofuran (5 mL) and cooled down to -78 °C. At this temperature, phosphorotriamine (30 μL, 0.32 mmol) was slowly added and the reaction lasted for 2 hours. Upon completion of the reaction, solid sodium bicarbonate (50 mg) was added to quench the reaction. The solid insoluble material was removed by filtration and the filtrate was subsequently evaporated to afford the target product 4-(tert-butoxycarbonylaminomethyl)benzyl bromide (300 mg, 95% yield).
123986-64-1
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187283-17-6
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Yield: 95%
Reaction Conditions:
with phosphorus tribromide in tetrahydrofuran at -78; for 2 h;
Steps:
91
A solution of 4-(N-t-Boc-aminomethyl)benzyl alcohol (250 mg, 1.1 mmol) in THF (5 mL) was treated with phosphorustribromide (30 uL, 0.32 mmol) at -78° C. for 2 h. After this period, the reaction was quenched with solid NaHCO3 (50 mg) and filtered to remove the solids and the filtrate was evaporated to give 4-(t-Boc-aminomethyl)benzyl bromide (300 mg, 95%).
References:
Eli Lilly and Company;Wayne State University;University of Hawaii US6680311, 2004, B1 Location in patent:Page/Page column 151
39895-56-2
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187283-17-6
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874-89-5
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187283-17-6
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24424-99-5
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187283-17-6
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17201-43-3
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187283-17-6
95 suppliers
$16.00/100mg