ChemicalBook CAS DataBase List 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene synthesis

8synthesis methods

Product Name:1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene
CAS Number:864725-22-4
Molecular formula:C9H5Cl2F3
Molecular Weight:241.04

2065-66-9
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130336-16-2 Synthesis

3',5'-DICHLORO-2,2,2-TRIFLUOROACETOPHENONE

130336-16-2
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1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

864725-22-4
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Yield:864725-22-4 79%

Reaction Conditions:

with potassium tert-butylate in tetrahydrofuran at 20 - 25; for 1.5 h;Product distribution / selectivity;

Steps:

S.8
To a suspension of methyl-triphenylphosphonium bromide (16.17 g, 25.27 mmol) and 3,5-dichloro-2,2,2-trifluoro acetophenone (10.0 g, 41 .15 mmol) in THF (65 mL) was added KOtBu (5.54 g, 49.38 mmol) in THF (28 mL) at 20-25°C. After 1 .5 h at room temp, the reaction was complete by GC. The mixture was separated between n- heptane and water. The organic layer was separated, washed with brine and the solvent was removed in vacuum. After cooling, the mixture was filtered from precipitating triphenylphosphine oxide to yield the title compound (8.78 g, 79%).¹H-NM R (360 M Hz, CDCI₃): δ = 5.82 (s, 1 H), 6.06 (s, 1 H), 7.32 (s, 2H), 7.38 (s, 1 H) ppm.

References:

BASF SE;KÖRBER, Karsten;KORDES, Markus;RACK, Michael;VON DEYN, Wolfgang;KAISER, Florian WO2012/59441, 2012, A2 Location in patent:Page/Page column 51

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1514-82-5 Synthesis