ChemicalBook CAS DataBase List fluoroMethyl 4-Methylbenzenesulfonate

fluoroMethyl 4-Methylbenzenesulfonate synthesis

5synthesis methods

Product Name:fluoroMethyl 4-Methylbenzenesulfonate
CAS Number:114435-86-8
Molecular formula:C8H9FO3S
Molecular Weight:204.22

Methylene ditosylate (100 mg, 0.28 mmol) and caesium fluoride (213 mg, 1.4 mmol) were dissolved in tert-amyl alcohol (5 mL) and irradiated in a microwave for 15 minutes at 90 °C. The reaction was allowed to cool and the tert-amyl alcohol was removed under reduced pressure, ice-cold diethyl ether was added and the suspension filtered, and then washed with plenty of ice-cold diethyl ether. The filtrate was concentrated under reduced pressure to yield Fluoromethyl 4-Methylbenzenesulfonate as a colourless oil (49 mg, 88% yield).

24124-59-2 Synthesis

1-methyl-4-[(4-methylphenyl)sulfonyloxymethoxysulfonyl]benzene

24124-59-2
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$50.00/100mg

114435-86-8
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$45.00/2.5mg

Yield:114435-86-8 88%

Reaction Conditions:

with cesium fluoride in tert-Amyl alcohol at 90; for 0.25 h;Microwave irradiation;Sealed tube;Temperature;Time;Concentration;

Steps:

Fluoromethyl 4-methylbenzenesulfonate²

Methylene ditosylate (100 mg, 0.28 mmol) and caesium fluoride (213 mg, 1.4 mmol) were dissolved in tert-amyl alcohol (5 mL) and irradiated in a microwave for 15 minutes at 90 °C. The reaction was allowed to cool and the tert-amyl alcohol was removed under reduced pressure, ice-cold diethyl ether was added and the suspension filtered, then washed with plenty of ice-cold diethyl ether. The filtrate was concentrated under reduced pressure to yield Fluoromethyl 4-methylbenzenesulfonate as a colourless oil (49 mg, 88% yield). ¹H NMR (500 MHz, CDCl₃) δ: 2.43 (s, 3H, ArCH₃), 5.72 (d, 2H, CH₂, J = 51.0 Hz), 7.35 (d, 2H, ArH, J = 8.0 Hz), 7.81 (d, 2H, ArH, J = 8.0 Hz); ¹³C (125 MHz, CDCl₃) δ: 21.67, 98.16 (d, J = 221 Hz), 127.87, 129.96, 133.77, 145.63; ¹⁹F (471 MHz, CDCl3) δ: -153.24 (t, J = 50.7 Hz).

References:

Brocklesby, Kayleigh L.;Waby, Jennifer S.;Cawthorne, Christopher;Smith, Graham [Tetrahedron Letters,2018,vol. 59,# 17,p. 1635 - 1637] Location in patent:supporting information

75-11-6
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$10.00/5g

16836-95-6
132 suppliers
$21.00/1g

114435-86-8
63 suppliers
$45.00/2.5mg

References

16836-95-6
132 suppliers
$21.00/1g

114435-86-8
63 suppliers
$45.00/2.5mg

References

24124-59-2 Synthesis

24124-59-2
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$50.00/100mg

455-16-3
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$52.50/10g

114435-86-8
63 suppliers
$45.00/2.5mg

References

104-15-4
707 suppliers
$133.00/500g

114435-86-8
63 suppliers
$45.00/2.5mg

References