ChemicalBook CAS DataBase List 3-BROMOPHENYL CYCLOPROPYL KETONE

3-BROMOPHENYL CYCLOPROPYL KETONE synthesis

5synthesis methods

Product Name:3-BROMOPHENYL CYCLOPROPYL KETONE
CAS Number:693774-26-4
Molecular formula:C10H9BrO
Molecular Weight:225.08

79134-92-2
6 suppliers
$512.00/1g

693774-26-4
25 suppliers
$206.80/1g

Yield:693774-26-4 87%

Reaction Conditions:

with Dess-Martin periodane in dichloromethane at 20; for 2 h;

Steps:

89 (3-Bromophenyl)(cyclopropyl)methanone

To a stirred solution of the alcohol of Preparation 88 (38 g, 168 mmol) in DCM (300 mL) was added Dess-Martin Periodinane (179 g, 422 mmol) at room temperature. The resulting reaction mixture was stirred at room temperature for 2 hours then diluted with saturated aq. sodium bicarbonate solution (250 mL) and 10% aq. sodium thiosulphate solution (250 mL). The aqueous layer was extracted with DCM (200 mL), the organic layer was washed with water (2 x 200 mL), brine (200 mL), dried over anhydrous Na₂SO₄ and concentrated under reduced pressure. The crude compound was purified by silica gel (100-200 mesh) column chromatography (2%-3% EtOAc in Hexane as an eluent) to afford the title compound (33 g, 87%) as an oil. 1H NMR (400 MHz,CHLOROFORM-d) d 8.14 (t, J=1.74 Hz, 1H), 7.93 (dt, J=7.74, 1.31 Hz, 1H), 7.67 - 7.71 (m, 1H), 7.36 (t, J=7.85 Hz, 1H), 2.62 (tt, J=7.82, 4.50 Hz, 1H), 1.26 (quin, J=3.84 Hz, 2H), 1.08 (dq, J=7.44, 3.59 Hz, 2H); LCMS (METHOD 5) (ESI): m/z: 225 [M+H+]; RT = 2.13 min; (ACQUITY UPLC BEH C18 column, 0.1% FA in water with MeCN).

References:

WO2020/182666,2020,A1 Location in patent:Page/Page column 83