1-(3,5-Dichloro-4-fluorophenyl)-2,2,2-trifluoroethanone synthesis
- Product Name:1-(3,5-Dichloro-4-fluorophenyl)-2,2,2-trifluoroethanone
- CAS Number:1190865-44-1
- Molecular formula:C8H2Cl2F4O
- Molecular Weight:261.0005
340-07-8
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17318-08-0
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1190865-44-1
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$6.00/1g
Yield:1190865-44-1 3.5 g
Reaction Conditions:
Stage #1:5-bromo-1,3-dichloro-2-fluorobenzene with TurboGrignard in tetrahydrofuran at 20; for 0.516667 h;Inert atmosphere;
Stage #2:N-(trifluoroacetyl)piperidine in tetrahydrofuran at 0 - 20; for 2 h;Inert atmosphere;
Steps:
1 Intermediate 3: 1-(4-chloro-3,5-difluorophenyl)-2,2,2-trifluoroethanone
Intermediate 3: 1-(4-chloro-3,5-difluorophenyl)-2,2,2-trifluoroethanone 5-Bromo-2-fluoro-1 ,3-dichlorobenzene (7.0 g, 28.7 mmol) was stirred at room temperature in THF (50 ml_) under argon and isopropylmagenesium chloride lithium chloride complex (24.3 ml_, 1.3 M in THF, 1.1 eq) was added over 1 min and stirred at RT for 30 min. To this was added piperidine trifluoroacetamide (5.6 ml_, 1.32 eq) over about 1 minute at 0°C and the reaction was stirred at room temperature for 2 h. The reaction was quenched with aqueous saturated NH4CI (50 ml_) and extracted with MTBE (2 x 50 ml_). Solvents were removed under reduced pressure and the crude product was purified using 12 g Redi-Sep column, eluting with 0 to 50% ethyl acetate in heptanes, to yield 3.5 g of 1-(4-chloro-3,5-difluorophenyl)-2,2,2- trifluoroethanone. H-NMR (400 MHz, CDCI3) δ ppm 8.06 (dd, 2H, J1 = 6.2 Hz, J2 = 0.9 Hz).
References:
AVISTA PHARMA SOLUTIONS;SPEAKE, Jason, D.;PERALES, Joe, B.;FAN, Weiming;ROLLAND, Solène, Clarisse WO2016/115315, 2016, A1 Location in patent:Page/Page column 30; 31
431-47-0
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17318-08-0
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1190865-44-1
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2729-34-2
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1190865-44-1
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17318-08-0
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$6.00/1g
1190865-44-1
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655-32-3
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1190865-44-1
128 suppliers
$6.00/1g