1-Ethynyl-2-fluorobenzene

Chemical Properties

clear yellow to brownish liquid

Uses

Employed in studies on the polymerization1 and cross-coupling2 of phenylacetylenes.

Uses

1-Ethynyl-2-fluorobenzene has been employed in the cross-coupling of phenylacetylenes. It may be used in the preparation of 3-(2-deoxy-β-D-ribofuranosyl)-6-(2-fluorophenyl)-2,3-dihydrofuro-[2,3-d]pyrimidin-2-one and 4-(2-fluorophenylethynyl)-3-methyl-5-phenylisoxazole.

Application

1-Ethynyl-2-fluorobenzene has been employed in the cross-coupling of phenylacetylenes. It may be used in the preparation of 3-(2-deoxy-β-D-ribofuranosyl)-6-(2-fluorophenyl)-2,3-dihydrofuro-[2,3-d]pyrimidin-2-one and 4-(2-fluorophenylethynyl)-3-methyl-5-phenylisoxazole.1-Ethynyl-2-fluorobenzene, a fluorinated benzene derivative, is a terminal alkyne.

General Description

1-Ethynyl-2-fluorobenzene, a fluorinated benzene derivative, is a terminal alkyne.

Synthesis

GENERAL STEPS: 1-(2,2-dibromovinyl)-2-fluorobenzene (1.0 eq.), Cs2CO3 (2.5 eq.) and DMSO (0.1 M) were mixed in a sealed tube and heated at 115 °C overnight according to a modified literature method [10]. Upon completion of the reaction, the reaction mixture was poured into brine (20 mL/mmol) to quench the reaction. Subsequently, the mixture was extracted with tert-butyl methyl ether (3 x 10 mL/mmol) and the combined organic layers were washed with brine (15 mL/mmol) and dried with Na2SO4. Finally, all volatiles were removed to give the crude product, which was purified by fast column chromatography to give the target product 1-ethynyl-2-fluorobenzene (S3).

References

[1] Tetrahedron, 2017, vol. 73, # 33, p. 5023 - 5028