Method for making ethynylated aromatic compounds

Details Method for making ethynylated aromatic compounds Method for making ethynylated aromatic compounds

1984-12-19

1988-11-01

Siegel, Alan

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

546176, 546264, 548518, 549 59, 549472, 564308, C07C 87452, C07D21512, C07D21336, C07D20700

Patent

active

047821841

ABSTRACT:
A method is disclosed for making amino-substituted ethynlated biphenyl compounds, which includes selectively nitrating symmetrically substituted biphenyl compounds, reacting the resulting nitro-substituted aromatic compound with a copper acetylide to replace the iodo substituents with ethynyl groups, and then reacting the ethynylated, nitro-substituted aromatic compound with hydrogen in the gas phase to reduce the nitro groups to amino groups. The preferred nitrating agent is nitronium trifluoromethanesulfonate, made by reaction of anhydrous nitric acid with trifluoromethanesulfonic anhydride in an anhydrous solvent.

REFERENCES:
Roberts et al., Basic Principles of Org Chem, 1964, pp. 800-803.
Wagner et al., Synthetic Organic Chem. (1965), pp. 654-657.
Rutledge Acetylenic Compounds (1968), pp. 86-87.
Coon, Journal of Org. Chem., vol. 38, No. 25, pp. 4243-4248 (1973).

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