2-bromo-1-(4-bromo-3-chlorophenyl)ethanone synthesis
- Product Name:2-bromo-1-(4-bromo-3-chlorophenyl)ethanone
- CAS Number:87427-57-4
- Molecular formula:C8H5Br2ClO
- Molecular Weight:312.39
3114-31-6
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Yield:87427-57-4 87%
Reaction Conditions:
with copper(ll) bromide in ethyl acetate at 80;Inert atmosphere;
Steps:
2-bromo-1-(4-bromo-3-chlorophenyl)ethanone
In a two necked round bottom flask equipped with a reflux condenser under an argon atmosphere was added CuBr2 (955 mg, 4.18 mmol) and EtOAc (10 mL). The suspension was stirred during 20 minutes. The 4-bromo-3- methylacetophenonone (500 mg, 2.14 mmol) pre-dissolved in EtO Ac (10 mL) was added to the mixture and heated at 80°C during one hour. A new equivalent of CuBr2 (460 mg, 2.06 mmol) was added and the reaction was stirred at 80°C overnight. The suspension was cooled down, filtered through a Celite pad and washed with EtO Ac. The filtrate was washed with a saturated NaHCO3 solution. The organic layer was dried over Na2SO4, filtered and evaporated under vacuum. Purification by silica gel flash chromatography (PE/EtOAc 4: 1) afforded the product (582 mg, 87%) as a yellow viscous oil. NMR (300 MHz, CDC13) δ 8.06 (d, J = 2.1 Hz, 1H, Har), 7.77 (d, J = 8.5 Hz, 1H, Har), 7.71 (dd, J = 8.4, 2.0 Hz, 1H, Har), 4.38 (s, 2H, CH2). 13C NMR (75 MHz, CDC13) δ 134.7 (CH), 131.0 (CH), 128.3 (CH), 30.4 (CH2). HRMS (ESI) [M+H]+ C8H6Br2ClO: Calcd. 310.8468 found 310.8455.
References:
WO2015/1024,2015,A1 Location in patent:Page/Page column 73
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