ChemicalBook CAS DataBase List t-Butyl 1-(4-bromophenyl)cyclopropylcarbamate

t-Butyl 1-(4-bromophenyl)cyclopropylcarbamate synthesis

5synthesis methods

Product Name:t-Butyl 1-(4-bromophenyl)cyclopropylcarbamate
CAS Number:360773-84-8
Molecular formula:C14H18BrNO2
Molecular Weight:312.2

24424-99-5 Synthesis

24424-99-5
825 suppliers
$13.50/25G

345965-54-0
87 suppliers
$65.00/100mg

t-Butyl 1-(4-bromophenyl)cyclopropylcarbamate

360773-84-8
75 suppliers
$29.00/250mg

Yield:360773-84-8 99%

Reaction Conditions:

with sodium carbonate in tetrahydrofuran;water at 20;

Steps:

53 tert-Butyl N-[1-(4-bromophenyl)cyclopropyl]carbamate
tert-Butyl N-[1-(4-bromophenyl)cyclopropyl]carbamate
In a 100-mL round bottom flask, 1-(4-bromophenyl)cyclopropan-1-amine (1 g, 4.48 mmol, 1.00 equiv) and di-tert-butyl dicarbonate (3.1 g, 13.49 mmol, 3.01 equiv) were mixed in tetrahydrofuran (20 mL), to which was added a solution of sodium bicarbonate (5 g, 59.5 mmol, 13.29 equiv) in water (10 mL) at room temperature.
The resulting solution was stirred overnight at room temperature.
After the reaction was done, the reaction mixture was extracted with ethyl acetate (3*10 mL) and the organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure.
The residue was purified in a silica gel column eluting with ethyl acetate in petroleum ether (10% to 50% gradient) to afford tert-butyl N-[1-(4-bromophenyl)cyclopropyl]carbamate (1.47 g, 99%) as light yellow solid. MS: m/z=255.7 [M+H-56]⁺.

References:

Merck Patent GmbH;GAILLARD, Pascale;SEENISAMY, Jeyaprakashnarayanan;LIU-BUJALSKI, Lesley;CALDWELL, Richard D.;POTNICK, Justin;QIU, Hui;NEAGU, Constantin;JONES, Reinaldo;WON, Annie Cho;GOUTOPOULOS, Andreas;SHERER, Brian A.;JOHNSON, Theresa L.;GARDBERG, Anna US2016/96834, 2016, A1 Location in patent:Paragraph 0390

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952289-92-8 Synthesis