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

345965-54-0

360773-84-8

The general procedure for the synthesis of tert-butyl [1-(4-bromophenyl)-cyclopropyl]carbamate from 1-(4-bromophenyl)cyclopropan-1-amine and di-tert-butyl dicarbonate was as follows: 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 eq.) were dissolved in tetrahydrofuran (20 mL). Subsequently, an aqueous solution of sodium bicarbonate (5 g, 59.5 mmol, 13.29 eq.) was slowly added to the reaction system (10 mL) at room temperature. The reaction mixture was stirred overnight at room temperature. After completion of the reaction, the reaction mixture was extracted with ethyl acetate (3 x 10 mL), the organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using ethyl acetate/petroleum ether (10% to 50% gradient) as eluent to afford tert-butyl [1-(4-bromophenyl)-cyclopropyl]carbamate (1.47 g, 99%) as a light yellow solid. Mass spectrometry (MS) analysis showed: m/z = 255.7 [M+H-56]+.

24424-99-5 Synthesis

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

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

360773-84-8
77 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