tert-butyl 4-(2-bromoethyl)phenylcarbamate synthesis

7synthesis methods

Product Name:tert-butyl 4-(2-bromoethyl)phenylcarbamate
CAS Number:218943-57-8
Molecular formula:C13H18BrNO2
Molecular Weight:300.19

24424-99-5 Synthesis

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4-(2-Bromoethyl)benzenamine Hydrobromide

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tert-butyl 4-(2-bromoethyl)phenylcarbamate

218943-57-8
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Yield:218943-57-8 88%

Reaction Conditions:

with triethylamine at 0 - 20; for 24 h;

Steps:

22

Di-tert-butyl dicarbonate (30.0 g 138 mmol) was added to an ice cooled mixture of p-aminophenylethyl bromide hydrobromide3 (36.0 g, 128 mmol) [(3) Tamai, T.; Tanaka, M.; Mukaiyama, H.; Hirabayashi, A.; Muranaka, H.; Sato. M.; Akahane, M. US 6353025] and triethylamine (10 niL) and the mixture was stirred at room temperature for 24 h. Solvents were removed and the pasty solid was treated with water and extracted with ethyl acetate. Evaporation of ethyl acetate gave a solid, which was purified by column chromatography using hexane-ethyl acetate. UV visible fractions were collected and evaporated to give a white solid. Yield 34.2 g (88%). MS: 324.2 (M+Na)

References:

WO2006/2873,2006,A2 Location in patent:Page/Page column 78